# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2a _database_code_depnum_ccdc_archive 'CCDC 917507' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H18' _chemical_formula_weight 354.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.095(10) _cell_length_b 4.8656(17) _cell_length_c 18.761(8) _cell_angle_alpha 90.00 _cell_angle_beta 122.671(5) _cell_angle_gamma 90.00 _cell_volume 1774.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 1579 _cell_measurement_theta_min 3.5428 _cell_measurement_theta_max 25.3295 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9851 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5444 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1550 _reflns_number_gt 1239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^2^+2.5251P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1550 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1576 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.20654(12) 0.0151(5) 0.05869(15) 0.0252(6) Uani 1 1 d . . . C2 C 0.27577(13) -0.0055(5) 0.08347(14) 0.0245(6) Uani 1 1 d . . . C3 C 0.32049(12) -0.1868(5) 0.14768(15) 0.0259(6) Uani 1 1 d . . . H1 H 0.3671 -0.2031 0.1641 0.031 Uiso 1 1 calc R . . C4 C 0.29467(12) -0.3441(5) 0.18731(14) 0.0233(6) Uani 1 1 d . . . H2 H 0.3240 -0.4699 0.2308 0.028 Uiso 1 1 calc R . . C5 C 0.22695(12) -0.3174(5) 0.16351(14) 0.0231(6) Uani 1 1 d . . . H3 H 0.2104 -0.4235 0.1914 0.028 Uiso 1 1 calc R . . C6 C 0.18245(13) -0.1369(5) 0.09909(15) 0.0252(6) Uani 1 1 d . . . H4 H 0.1360 -0.1194 0.0834 0.030 Uiso 1 1 calc R . . C7 C 0.16924(12) 0.2144(5) -0.01331(15) 0.0250(6) Uani 1 1 d . A . C8 C 0.21653(11) 0.3108(5) -0.02787(14) 0.0236(6) Uani 1 1 d . . . C9 C 0.09469(12) 0.2745(5) -0.06044(15) 0.0255(6) Uani 1 1 d . . . C10 C 0.0679(2) 0.5440(10) -0.0889(3) 0.0248(12) Uani 0.504(4) 1 d P A 1 H5 H 0.0987 0.6923 -0.0766 0.030 Uiso 0.504(4) 1 calc PR A 1 C11 C -0.0026(2) 0.5935(9) -0.1342(3) 0.0236(11) Uani 0.504(4) 1 d P A 1 H6 H -0.0199 0.7740 -0.1530 0.028 Uiso 0.504(4) 1 calc PR A 1 C12 C -0.04720(12) 0.3775(5) -0.15156(15) 0.0248(6) Uani 1 1 d . . . H7 H -0.0950 0.4128 -0.1783 0.030 Uiso 0.504(4) 1 calc PR A 1 H8 H -0.0952 0.4132 -0.1831 0.030 Uiso 0.496(4) 1 calc PR A 2 C13 C -0.0236(2) 0.1146(10) -0.1308(3) 0.0261(12) Uani 0.504(4) 1 d P A 1 H9 H -0.0551 -0.0334 -0.1469 0.031 Uiso 0.504(4) 1 calc PR A 1 C14 C 0.0466(2) 0.0634(10) -0.0862(3) 0.0275(12) Uani 0.504(4) 1 d P A 1 H10 H 0.0623 -0.1211 -0.0727 0.033 Uiso 0.504(4) 1 calc PR A 1 C15 C 0.0576(2) 0.2800(10) -0.1459(3) 0.0249(12) Uani 0.496(4) 1 d P A 2 H11 H 0.0799 0.2506 -0.1755 0.030 Uiso 0.496(4) 1 calc PR A 2 C16 C -0.0129(2) 0.3283(10) -0.1910(3) 0.0255(12) Uani 0.496(4) 1 d P A 2 H12 H -0.0380 0.3271 -0.2511 0.031 Uiso 0.496(4) 1 calc PR A 2 C17 C -0.0080(2) 0.3732(9) -0.0606(3) 0.0235(12) Uani 0.496(4) 1 d P A 2 H13 H -0.0303 0.4061 -0.0312 0.028 Uiso 0.496(4) 1 calc PR A 2 C18 C 0.0621(2) 0.3215(10) -0.0155(3) 0.0233(12) Uani 0.496(4) 1 d P A 2 H14 H 0.0879 0.3176 0.0446 0.028 Uiso 0.496(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0306(13) 0.0173(13) 0.0249(13) -0.0020(10) 0.0132(11) 0.0017(10) C2 0.0426(15) 0.0144(12) 0.0234(12) -0.0040(9) 0.0223(11) -0.0057(10) C3 0.0275(13) 0.0230(13) 0.0290(13) -0.0072(10) 0.0165(11) -0.0051(10) C4 0.0274(13) 0.0171(12) 0.0227(12) -0.0003(9) 0.0118(10) -0.0015(9) C5 0.0291(13) 0.0183(12) 0.0227(12) -0.0005(9) 0.0145(11) -0.0028(10) C6 0.0286(13) 0.0200(13) 0.0247(12) -0.0008(10) 0.0130(11) 0.0006(10) C7 0.0270(13) 0.0203(13) 0.0273(13) -0.0037(10) 0.0144(11) -0.0020(10) C8 0.0230(12) 0.0231(13) 0.0241(12) -0.0099(10) 0.0124(10) -0.0036(10) C9 0.0198(12) 0.0241(13) 0.0307(14) -0.0047(10) 0.0124(11) 0.0000(10) C10 0.023(2) 0.029(3) 0.028(3) -0.009(2) 0.017(2) -0.009(2) C11 0.025(2) 0.020(3) 0.025(3) -0.0023(19) 0.014(2) 0.002(2) C12 0.0181(12) 0.0243(14) 0.0289(13) 0.0023(10) 0.0106(10) 0.0022(10) C13 0.023(2) 0.023(3) 0.027(3) 0.001(2) 0.011(2) -0.0042(19) C14 0.023(2) 0.023(3) 0.031(3) -0.001(2) 0.011(2) 0.003(2) C15 0.032(3) 0.019(3) 0.031(3) -0.003(2) 0.022(2) -0.005(2) C16 0.030(3) 0.020(3) 0.023(2) 0.0024(19) 0.011(2) -0.002(2) C17 0.020(2) 0.022(3) 0.031(3) 0.001(2) 0.016(2) -0.0035(19) C18 0.021(2) 0.021(3) 0.025(2) -0.0013(19) 0.011(2) 0.0000(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.373(3) . ? C1 C2 1.407(3) . ? C1 C7 1.500(3) . ? C2 C3 1.397(3) . ? C2 C8 1.489(3) 7 ? C3 C4 1.405(3) . ? C3 H1 0.9500 . ? C4 C5 1.381(3) . ? C4 H2 0.9500 . ? C5 C6 1.395(3) . ? C5 H3 0.9500 . ? C6 H4 0.9500 . ? C7 C8 1.345(3) . ? C7 C9 1.479(3) . ? C8 C8 1.445(5) 7 ? C8 C2 1.489(3) 7 ? C9 C15 1.350(5) . ? C9 C14 1.394(5) . ? C9 C18 1.419(5) . ? C9 C10 1.425(6) . ? C10 C11 1.392(6) . ? C10 H5 0.9500 . ? C11 C12 1.382(5) . ? C11 H6 0.9500 . ? C12 C13 1.362(5) . ? C12 C16 1.365(5) . ? C12 C17 1.436(5) . ? C12 H7 0.9500 . ? C12 H8 0.9500 . ? C13 C14 1.387(7) . ? C13 H9 0.9500 . ? C14 H10 0.9500 . ? C15 C16 1.391(7) . ? C15 H11 0.9500 . ? C16 H12 0.9500 . ? C17 C18 1.385(6) . ? C17 H13 0.9500 . ? C18 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.4(2) . . ? C6 C1 C7 129.7(2) . . ? C2 C1 C7 110.0(2) . . ? C3 C2 C1 120.6(2) . . ? C3 C2 C8 133.9(2) . 7 ? C1 C2 C8 105.5(2) . 7 ? C2 C3 C4 118.2(2) . . ? C2 C3 H1 120.9 . . ? C4 C3 H1 120.9 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H2 119.7 . . ? C3 C4 H2 119.7 . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H3 119.5 . . ? C6 C5 H3 119.5 . . ? C1 C6 C5 119.2(2) . . ? C1 C6 H4 120.4 . . ? C5 C6 H4 120.4 . . ? C8 C7 C9 128.3(2) . . ? C8 C7 C1 105.9(2) . . ? C9 C7 C1 125.7(2) . . ? C7 C8 C8 112.3(3) . 7 ? C7 C8 C2 141.4(2) . 7 ? C8 C8 C2 106.4(2) 7 7 ? C15 C9 C14 74.2(3) . . ? C15 C9 C18 120.1(3) . . ? C14 C9 C18 75.2(3) . . ? C15 C9 C10 70.6(3) . . ? C14 C9 C10 116.4(3) . . ? C18 C9 C10 79.1(3) . . ? C15 C9 C7 120.1(3) . . ? C14 C9 C7 121.0(3) . . ? C18 C9 C7 119.8(3) . . ? C10 C9 C7 122.4(3) . . ? C11 C10 C9 121.1(4) . . ? C11 C10 H5 119.4 . . ? C9 C10 H5 119.4 . . ? C12 C11 C10 119.3(4) . . ? C12 C11 H6 120.3 . . ? C10 C11 H6 120.3 . . ? C13 C12 C16 74.3(3) . . ? C13 C12 C11 121.0(3) . . ? C16 C12 C11 71.6(3) . . ? C13 C12 C17 75.5(3) . . ? C16 C12 C17 117.6(3) . . ? C11 C12 C17 79.6(3) . . ? C13 C12 H7 119.5 . . ? C16 C12 H7 126.5 . . ? C11 C12 H7 119.5 . . ? C17 C12 H7 116.0 . . ? C13 C12 H8 120.2 . . ? C16 C12 H8 121.2 . . ? C11 C12 H8 118.6 . . ? C17 C12 H8 121.2 . . ? H7 C12 H8 5.3 . . ? C12 C13 C14 119.9(4) . . ? C12 C13 H9 120.1 . . ? C14 C13 H9 120.1 . . ? C13 C14 C9 122.0(4) . . ? C13 C14 H10 119.0 . . ? C9 C14 H10 119.0 . . ? C9 C15 C16 120.6(4) . . ? C9 C15 H11 119.7 . . ? C16 C15 H11 119.7 . . ? C12 C16 C15 122.1(4) . . ? C12 C16 H12 118.9 . . ? C15 C16 H12 118.9 . . ? C18 C17 C12 120.5(4) . . ? C18 C17 H13 119.8 . . ? C12 C17 H13 119.8 . . ? C17 C18 C9 119.1(4) . . ? C17 C18 H14 120.5 . . ? C9 C18 H14 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.0(3) . . . . ? C7 C1 C2 C3 -177.7(2) . . . . ? C6 C1 C2 C8 -178.9(2) . . . 7 ? C7 C1 C2 C8 1.4(3) . . . 7 ? C1 C2 C3 C4 -0.8(3) . . . . ? C8 C2 C3 C4 -179.7(2) 7 . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? C7 C1 C6 C5 177.9(2) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C6 C1 C7 C8 178.9(2) . . . . ? C2 C1 C7 C8 -1.5(3) . . . . ? C6 C1 C7 C9 -4.5(4) . . . . ? C2 C1 C7 C9 175.2(2) . . . . ? C9 C7 C8 C8 -175.6(2) . . . 7 ? C1 C7 C8 C8 1.0(3) . . . 7 ? C9 C7 C8 C2 4.2(5) . . . 7 ? C1 C7 C8 C2 -179.2(3) . . . 7 ? C8 C7 C9 C15 43.1(4) . . . . ? C1 C7 C9 C15 -132.8(3) . . . . ? C8 C7 C9 C14 132.0(3) . . . . ? C1 C7 C9 C14 -43.9(4) . . . . ? C8 C7 C9 C18 -138.0(3) . . . . ? C1 C7 C9 C18 46.1(4) . . . . ? C8 C7 C9 C10 -41.9(4) . . . . ? C1 C7 C9 C10 142.1(3) . . . . ? C15 C9 C10 C11 65.0(4) . . . . ? C14 C9 C10 C11 4.8(6) . . . . ? C18 C9 C10 C11 -62.5(4) . . . . ? C7 C9 C10 C11 179.0(3) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? C10 C11 C12 C13 -5.2(6) . . . . ? C10 C11 C12 C16 -63.1(4) . . . . ? C10 C11 C12 C17 60.7(4) . . . . ? C16 C12 C13 C14 61.4(5) . . . . ? C11 C12 C13 C14 4.8(6) . . . . ? C17 C12 C13 C14 -63.3(5) . . . . ? C12 C13 C14 C9 0.7(7) . . . . ? C15 C9 C14 C13 -63.7(5) . . . . ? C18 C9 C14 C13 64.2(5) . . . . ? C10 C9 C14 C13 -5.4(6) . . . . ? C7 C9 C14 C13 -179.6(4) . . . . ? C14 C9 C15 C16 61.1(4) . . . . ? C18 C9 C15 C16 -0.8(6) . . . . ? C10 C9 C15 C16 -65.0(4) . . . . ? C7 C9 C15 C16 178.1(3) . . . . ? C13 C12 C16 C15 -64.9(5) . . . . ? C11 C12 C16 C15 66.1(5) . . . . ? C17 C12 C16 C15 -1.1(6) . . . . ? C9 C15 C16 C12 1.4(7) . . . . ? C13 C12 C17 C18 63.4(5) . . . . ? C16 C12 C17 C18 0.2(6) . . . . ? C11 C12 C17 C18 -62.6(4) . . . . ? C12 C17 C18 C9 0.4(6) . . . . ? C15 C9 C18 C17 -0.1(6) . . . . ? C14 C9 C18 C17 -61.5(4) . . . . ? C10 C9 C18 C17 59.8(4) . . . . ? C7 C9 C18 C17 -179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.723 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.054 data_2b _database_code_depnum_ccdc_archive 'CCDC 917508' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H14 F12' _chemical_formula_weight 626.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.283(9) _cell_length_b 12.769(18) _cell_length_c 13.17(2) _cell_angle_alpha 80.39(9) _cell_angle_beta 77.65(11) _cell_angle_gamma 71.77(10) _cell_volume 1285(3) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 2537 _cell_measurement_theta_min 3.1853 _cell_measurement_theta_max 25.0041 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8312 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.1412 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4401 _reflns_number_gt 1923 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1912P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4401 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1760 _refine_ls_R_factor_gt 0.1086 _refine_ls_wR_factor_ref 0.3426 _refine_ls_wR_factor_gt 0.2672 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2493(8) -0.1113(5) 0.6245(5) 0.0326(15) Uani 1 1 d . . . C2 C 0.2350(8) -0.1579(5) 0.7260(5) 0.0327(15) Uani 1 1 d . . . H1 H 0.2368 -0.1179 0.7802 0.039 Uiso 1 1 calc R . . C3 C 0.2174(8) -0.2663(5) 0.7494(5) 0.0348(15) Uani 1 1 d . . . H2 H 0.2041 -0.2987 0.8200 0.042 Uiso 1 1 calc R . . C4 C 0.2195(8) -0.3267(5) 0.6681(5) 0.0365(16) Uani 1 1 d . . . C5 C 0.2308(8) -0.2816(5) 0.5645(5) 0.0342(15) Uani 1 1 d . . . H3 H 0.2262 -0.3218 0.5111 0.041 Uiso 1 1 calc R . . C6 C 0.2496(8) -0.1720(5) 0.5412(5) 0.0361(16) Uani 1 1 d . . . C7 C 0.2665(8) -0.1022(5) 0.4388(5) 0.0360(16) Uani 1 1 d . . . C8 C 0.2723(7) -0.0010(5) 0.4602(5) 0.0314(15) Uani 1 1 d . . . C9 C 0.2607(8) 0.0005(5) 0.5725(5) 0.0337(15) Uani 1 1 d . . . C10 C 0.2512(8) 0.1032(5) 0.5975(5) 0.0356(15) Uani 1 1 d . . . C11 C 0.2667(8) 0.1740(5) 0.4952(5) 0.0312(15) Uani 1 1 d . . . C12 C 0.2750(8) 0.2842(5) 0.4756(5) 0.0367(16) Uani 1 1 d . . . H4 H 0.2688 0.3251 0.5310 0.044 Uiso 1 1 calc R . . C13 C 0.2932(8) 0.3328(5) 0.3686(6) 0.0367(16) Uani 1 1 d . . . C14 C 0.3086(8) 0.2729(5) 0.2867(5) 0.0353(15) Uani 1 1 d . . . H5 H 0.3260 0.3058 0.2166 0.042 Uiso 1 1 calc R . . C15 C 0.2984(8) 0.1612(5) 0.3080(5) 0.0360(16) Uani 1 1 d . . . H6 H 0.3048 0.1205 0.2523 0.043 Uiso 1 1 calc R . . C16 C 0.2786(8) 0.1121(5) 0.4123(5) 0.0337(15) Uani 1 1 d . . . C17 C 0.1964(10) -0.4420(6) 0.7015(6) 0.0451(18) Uani 1 1 d . . . F1 F 0.3039(5) -0.5036(3) 0.7654(3) 0.0493(11) Uani 1 1 d . . . F2 F 0.0352(5) -0.4398(3) 0.7512(3) 0.0500(11) Uani 1 1 d . . . F3 F 0.2281(6) -0.4997(3) 0.6173(3) 0.0541(12) Uani 1 1 d . . . C18 C 0.2910(9) 0.4537(5) 0.3502(6) 0.0407(17) Uani 1 1 d . . . F4 F 0.1333(5) 0.5208(3) 0.3918(3) 0.0491(11) Uani 1 1 d . . . F5 F 0.4057(5) 0.4755(3) 0.3969(3) 0.0428(10) Uani 1 1 d . . . F6 F 0.3197(5) 0.4896(3) 0.2492(3) 0.0499(11) Uani 1 1 d . . . C19 C 0.2693(8) -0.1318(5) 0.3345(5) 0.0328(15) Uani 1 1 d . . . C20 C 0.3677(8) -0.2375(5) 0.3008(6) 0.0384(17) Uani 1 1 d . . . H7 H 0.4271 -0.2935 0.3480 0.046 Uiso 1 1 calc R . . C21 C 0.3771(8) -0.2589(5) 0.1999(5) 0.0360(16) Uani 1 1 d . . . H8 H 0.4451 -0.3288 0.1778 0.043 Uiso 1 1 calc R . . C22 C 0.2872(9) -0.1782(5) 0.1301(5) 0.0369(16) Uani 1 1 d . . . C23 C 0.1854(8) -0.0756(5) 0.1623(5) 0.0394(17) Uani 1 1 d . . . H9 H 0.1228 -0.0214 0.1152 0.047 Uiso 1 1 calc R . . C24 C 0.1755(8) -0.0526(5) 0.2640(5) 0.0360(16) Uani 1 1 d . . . H10 H 0.1050 0.0169 0.2859 0.043 Uiso 1 1 calc R . . C25 C 0.3038(9) -0.1999(5) 0.0190(6) 0.0420(17) Uani 1 1 d . . . F7 F 0.1523(5) -0.1510(3) -0.0197(3) 0.0488(11) Uani 1 1 d . . . F8 F 0.3498(5) -0.3075(3) 0.0045(3) 0.0503(11) Uani 1 1 d . . . F9 F 0.4201(5) -0.1544(3) -0.0471(3) 0.0486(11) Uani 1 1 d . . . C26 C 0.2258(8) 0.1441(5) 0.6990(5) 0.0347(15) Uani 1 1 d . . . C27 C 0.3157(8) 0.0846(5) 0.7790(5) 0.0339(15) Uani 1 1 d . . . H11 H 0.3959 0.0141 0.7677 0.041 Uiso 1 1 calc R . . C28 C 0.2919(8) 0.1251(5) 0.8756(5) 0.0364(16) Uani 1 1 d . . . H12 H 0.3548 0.0830 0.9285 0.044 Uiso 1 1 calc R . . C29 C 0.1719(8) 0.2305(5) 0.8922(5) 0.0341(15) Uani 1 1 d . . . C30 C 0.0780(8) 0.2901(5) 0.8153(5) 0.0374(16) Uani 1 1 d . . . H13 H -0.0040 0.3599 0.8272 0.045 Uiso 1 1 calc R . . C31 C 0.1041(8) 0.2471(5) 0.7193(5) 0.0360(16) Uani 1 1 d . . . H14 H 0.0384 0.2883 0.6672 0.043 Uiso 1 1 calc R . . C32 C 0.1523(9) 0.2786(6) 0.9916(6) 0.0465(19) Uani 1 1 d . . . F10 F 0.1660(5) 0.2005(3) 1.0755(3) 0.0507(11) Uani 1 1 d . . . F11 F -0.0059(5) 0.3554(3) 1.0148(3) 0.0499(11) Uani 1 1 d . . . F12 F 0.2727(5) 0.3324(3) 0.9899(3) 0.0528(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(4) 0.023(3) 0.036(4) -0.006(3) -0.004(3) -0.003(3) C2 0.033(3) 0.021(3) 0.039(4) 0.000(3) -0.002(3) -0.005(3) C3 0.041(4) 0.024(3) 0.038(4) -0.002(3) -0.003(3) -0.011(3) C4 0.037(4) 0.022(3) 0.043(4) -0.004(3) 0.007(3) -0.007(3) C5 0.032(4) 0.019(3) 0.045(4) -0.004(3) 0.001(3) -0.002(3) C6 0.033(4) 0.030(3) 0.046(4) -0.003(3) -0.003(3) -0.012(3) C7 0.031(4) 0.017(3) 0.053(4) -0.004(3) 0.003(3) -0.005(3) C8 0.026(3) 0.023(3) 0.040(4) -0.007(3) 0.005(3) -0.006(3) C9 0.031(4) 0.021(3) 0.044(4) -0.004(3) -0.001(3) -0.004(3) C10 0.034(4) 0.023(3) 0.046(4) 0.000(3) -0.004(3) -0.007(3) C11 0.035(4) 0.018(3) 0.034(4) 0.000(3) -0.004(3) -0.002(3) C12 0.034(4) 0.024(3) 0.049(4) -0.012(3) 0.001(3) -0.005(3) C13 0.026(3) 0.021(3) 0.058(4) -0.007(3) 0.005(3) -0.005(3) C14 0.029(3) 0.029(3) 0.044(4) -0.007(3) 0.001(3) -0.005(3) C15 0.037(4) 0.020(3) 0.046(4) -0.006(3) -0.005(3) -0.002(3) C16 0.034(4) 0.019(3) 0.043(4) 0.000(3) -0.006(3) -0.001(3) C17 0.046(4) 0.033(4) 0.056(5) -0.015(3) -0.007(4) -0.008(3) F1 0.047(2) 0.026(2) 0.072(3) 0.007(2) -0.018(2) -0.0063(18) F2 0.039(2) 0.034(2) 0.072(3) -0.002(2) 0.0025(19) -0.0126(18) F3 0.086(3) 0.033(2) 0.047(3) -0.0067(18) 0.000(2) -0.029(2) C18 0.049(4) 0.026(4) 0.044(4) 0.001(3) -0.009(3) -0.009(3) F4 0.043(2) 0.022(2) 0.074(3) -0.0086(19) -0.004(2) -0.0002(17) F5 0.039(2) 0.027(2) 0.060(3) -0.0081(18) -0.0047(19) -0.0074(17) F6 0.068(3) 0.034(2) 0.048(3) 0.0001(19) -0.006(2) -0.019(2) C19 0.034(4) 0.026(3) 0.038(4) -0.008(3) 0.004(3) -0.012(3) C20 0.031(4) 0.027(3) 0.054(5) 0.003(3) -0.009(3) -0.007(3) C21 0.040(4) 0.025(3) 0.042(4) -0.007(3) -0.002(3) -0.009(3) C22 0.043(4) 0.024(3) 0.046(4) -0.012(3) 0.000(3) -0.014(3) C23 0.038(4) 0.029(4) 0.050(4) 0.000(3) -0.011(3) -0.009(3) C24 0.035(4) 0.025(3) 0.048(4) -0.001(3) -0.016(3) -0.005(3) C25 0.040(4) 0.029(4) 0.053(5) 0.006(3) -0.011(3) -0.008(3) F7 0.046(2) 0.049(3) 0.049(3) -0.012(2) -0.0052(19) -0.010(2) F8 0.070(3) 0.034(2) 0.050(3) -0.0133(19) -0.008(2) -0.017(2) F9 0.045(2) 0.048(2) 0.049(3) -0.004(2) 0.0010(19) -0.0156(19) C26 0.029(3) 0.026(3) 0.048(4) -0.012(3) -0.003(3) -0.006(3) C27 0.030(4) 0.025(3) 0.041(4) -0.008(3) 0.000(3) -0.003(3) C28 0.033(4) 0.030(4) 0.044(4) -0.008(3) -0.001(3) -0.007(3) C29 0.038(4) 0.027(3) 0.035(4) -0.010(3) 0.001(3) -0.007(3) C30 0.037(4) 0.024(3) 0.047(4) -0.006(3) 0.000(3) -0.007(3) C31 0.031(4) 0.024(3) 0.048(4) -0.001(3) -0.003(3) -0.005(3) C32 0.034(4) 0.028(4) 0.066(5) -0.009(4) 0.002(3) 0.003(3) F10 0.064(3) 0.039(2) 0.048(3) -0.001(2) -0.008(2) -0.016(2) F11 0.053(3) 0.040(2) 0.053(3) -0.0183(19) 0.0033(19) -0.0078(19) F12 0.052(3) 0.046(2) 0.068(3) -0.018(2) -0.004(2) -0.024(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.366(9) . ? C1 C6 1.444(9) . ? C1 C9 1.500(9) . ? C2 C3 1.413(8) . ? C2 H1 0.9500 . ? C3 C4 1.415(9) . ? C3 H2 0.9500 . ? C4 C5 1.386(9) . ? C4 C17 1.524(9) . ? C5 C6 1.432(9) . ? C5 H3 0.9500 . ? C6 C7 1.494(9) . ? C7 C8 1.385(9) . ? C7 C19 1.478(9) . ? C8 C9 1.464(9) . ? C8 C16 1.489(8) . ? C9 C10 1.380(9) . ? C10 C26 1.465(9) . ? C10 C11 1.497(9) . ? C11 C12 1.409(9) . ? C11 C16 1.421(9) . ? C12 C13 1.438(9) . ? C12 H4 0.9500 . ? C13 C14 1.385(9) . ? C13 C18 1.517(9) . ? C14 C15 1.433(9) . ? C14 H5 0.9500 . ? C15 C16 1.410(9) . ? C15 H6 0.9500 . ? C17 F1 1.335(8) . ? C17 F2 1.349(8) . ? C17 F3 1.367(8) . ? C18 F6 1.328(8) . ? C18 F5 1.352(8) . ? C18 F4 1.376(8) . ? C19 C24 1.411(9) . ? C19 C20 1.428(9) . ? C20 C21 1.381(9) . ? C20 H7 0.9500 . ? C21 C22 1.400(9) . ? C21 H8 0.9500 . ? C22 C23 1.396(9) . ? C22 C25 1.504(10) . ? C23 C24 1.399(10) . ? C23 H9 0.9500 . ? C24 H10 0.9500 . ? C25 F8 1.341(8) . ? C25 F9 1.360(8) . ? C25 F7 1.379(7) . ? C26 C27 1.399(9) . ? C26 C31 1.411(8) . ? C27 C28 1.404(9) . ? C27 H11 0.9500 . ? C28 C29 1.420(9) . ? C28 H12 0.9500 . ? C29 C30 1.386(9) . ? C29 C32 1.494(10) . ? C30 C31 1.409(9) . ? C30 H13 0.9500 . ? C31 H14 0.9500 . ? C32 F10 1.357(8) . ? C32 F12 1.371(9) . ? C32 F11 1.378(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.9(6) . . ? C2 C1 C9 133.8(6) . . ? C6 C1 C9 105.3(5) . . ? C1 C2 C3 119.2(6) . . ? C1 C2 H1 120.4 . . ? C3 C2 H1 120.4 . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H2 119.9 . . ? C4 C3 H2 119.9 . . ? C5 C4 C3 122.3(6) . . ? C5 C4 C17 121.4(6) . . ? C3 C4 C17 116.2(6) . . ? C4 C5 C6 117.2(6) . . ? C4 C5 H3 121.4 . . ? C6 C5 H3 121.4 . . ? C5 C6 C1 120.2(6) . . ? C5 C6 C7 129.9(6) . . ? C1 C6 C7 109.9(6) . . ? C8 C7 C19 125.9(6) . . ? C8 C7 C6 106.6(6) . . ? C19 C7 C6 127.5(6) . . ? C7 C8 C9 111.1(6) . . ? C7 C8 C16 143.7(6) . . ? C9 C8 C16 105.1(5) . . ? C10 C9 C8 112.6(6) . . ? C10 C9 C1 140.2(6) . . ? C8 C9 C1 107.0(5) . . ? C9 C10 C26 131.0(6) . . ? C9 C10 C11 105.4(6) . . ? C26 C10 C11 123.6(6) . . ? C12 C11 C16 121.3(6) . . ? C12 C11 C10 128.9(6) . . ? C16 C11 C10 109.8(6) . . ? C11 C12 C13 117.7(6) . . ? C11 C12 H4 121.2 . . ? C13 C12 H4 121.2 . . ? C14 C13 C12 121.7(6) . . ? C14 C13 C18 121.8(6) . . ? C12 C13 C18 116.5(6) . . ? C13 C14 C15 119.9(6) . . ? C13 C14 H5 120.0 . . ? C15 C14 H5 120.0 . . ? C16 C15 C14 119.4(6) . . ? C16 C15 H6 120.3 . . ? C14 C15 H6 120.3 . . ? C15 C16 C11 119.9(6) . . ? C15 C16 C8 132.9(6) . . ? C11 C16 C8 107.1(5) . . ? F1 C17 F2 106.9(6) . . ? F1 C17 F3 106.3(6) . . ? F2 C17 F3 106.4(6) . . ? F1 C17 C4 112.5(6) . . ? F2 C17 C4 113.0(5) . . ? F3 C17 C4 111.3(6) . . ? F6 C18 F5 108.2(6) . . ? F6 C18 F4 106.5(5) . . ? F5 C18 F4 104.7(6) . . ? F6 C18 C13 112.4(6) . . ? F5 C18 C13 113.4(5) . . ? F4 C18 C13 111.1(6) . . ? C24 C19 C20 118.3(6) . . ? C24 C19 C7 119.4(6) . . ? C20 C19 C7 122.3(6) . . ? C21 C20 C19 120.4(6) . . ? C21 C20 H7 119.8 . . ? C19 C20 H7 119.8 . . ? C20 C21 C22 120.5(6) . . ? C20 C21 H8 119.7 . . ? C22 C21 H8 119.7 . . ? C23 C22 C21 120.1(7) . . ? C23 C22 C25 119.5(6) . . ? C21 C22 C25 120.3(6) . . ? C22 C23 C24 119.9(6) . . ? C22 C23 H9 120.0 . . ? C24 C23 H9 120.0 . . ? C23 C24 C19 120.6(6) . . ? C23 C24 H10 119.7 . . ? C19 C24 H10 119.7 . . ? F8 C25 F9 107.2(6) . . ? F8 C25 F7 106.3(6) . . ? F9 C25 F7 104.0(5) . . ? F8 C25 C22 114.7(5) . . ? F9 C25 C22 111.8(6) . . ? F7 C25 C22 112.2(6) . . ? C27 C26 C31 117.4(6) . . ? C27 C26 C10 123.0(6) . . ? C31 C26 C10 119.6(6) . . ? C26 C27 C28 122.5(6) . . ? C26 C27 H11 118.7 . . ? C28 C27 H11 118.7 . . ? C27 C28 C29 118.5(6) . . ? C27 C28 H12 120.7 . . ? C29 C28 H12 120.7 . . ? C30 C29 C28 120.2(6) . . ? C30 C29 C32 120.2(6) . . ? C28 C29 C32 119.5(6) . . ? C29 C30 C31 120.0(6) . . ? C29 C30 H13 120.0 . . ? C31 C30 H13 120.0 . . ? C30 C31 C26 121.3(6) . . ? C30 C31 H14 119.3 . . ? C26 C31 H14 119.3 . . ? F10 C32 F12 106.2(6) . . ? F10 C32 F11 106.1(6) . . ? F12 C32 F11 105.8(5) . . ? F10 C32 C29 112.5(6) . . ? F12 C32 C29 113.4(6) . . ? F11 C32 C29 112.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(9) . . . . ? C9 C1 C2 C3 176.4(6) . . . . ? C1 C2 C3 C4 1.7(9) . . . . ? C2 C3 C4 C5 -2.9(10) . . . . ? C2 C3 C4 C17 -178.9(6) . . . . ? C3 C4 C5 C6 3.2(9) . . . . ? C17 C4 C5 C6 179.0(6) . . . . ? C4 C5 C6 C1 -2.4(9) . . . . ? C4 C5 C6 C7 179.4(6) . . . . ? C2 C1 C6 C5 1.4(9) . . . . ? C9 C1 C6 C5 -176.7(5) . . . . ? C2 C1 C6 C7 179.9(5) . . . . ? C9 C1 C6 C7 1.8(7) . . . . ? C5 C6 C7 C8 177.0(6) . . . . ? C1 C6 C7 C8 -1.3(7) . . . . ? C5 C6 C7 C19 -0.6(11) . . . . ? C1 C6 C7 C19 -178.9(6) . . . . ? C19 C7 C8 C9 177.9(6) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C19 C7 C8 C16 1.7(13) . . . . ? C6 C7 C8 C16 -176.0(8) . . . . ? C7 C8 C9 C10 -174.8(5) . . . . ? C16 C8 C9 C10 2.9(7) . . . . ? C7 C8 C9 C1 0.9(7) . . . . ? C16 C8 C9 C1 178.6(5) . . . . ? C2 C1 C9 C10 -5.6(14) . . . . ? C6 C1 C9 C10 172.1(8) . . . . ? C2 C1 C9 C8 -179.4(7) . . . . ? C6 C1 C9 C8 -1.7(6) . . . . ? C8 C9 C10 C26 175.0(6) . . . . ? C1 C9 C10 C26 1.4(14) . . . . ? C8 C9 C10 C11 -3.1(7) . . . . ? C1 C9 C10 C11 -176.7(7) . . . . ? C9 C10 C11 C12 -175.9(6) . . . . ? C26 C10 C11 C12 5.8(10) . . . . ? C9 C10 C11 C16 2.2(7) . . . . ? C26 C10 C11 C16 -176.1(6) . . . . ? C16 C11 C12 C13 1.0(9) . . . . ? C10 C11 C12 C13 178.8(6) . . . . ? C11 C12 C13 C14 -2.3(9) . . . . ? C11 C12 C13 C18 176.5(6) . . . . ? C12 C13 C14 C15 3.0(9) . . . . ? C18 C13 C14 C15 -175.8(6) . . . . ? C13 C14 C15 C16 -2.2(9) . . . . ? C14 C15 C16 C11 0.9(9) . . . . ? C14 C15 C16 C8 -176.6(6) . . . . ? C12 C11 C16 C15 -0.3(9) . . . . ? C10 C11 C16 C15 -178.5(5) . . . . ? C12 C11 C16 C8 177.8(5) . . . . ? C10 C11 C16 C8 -0.4(7) . . . . ? C7 C8 C16 C15 -7.3(14) . . . . ? C9 C8 C16 C15 176.4(6) . . . . ? C7 C8 C16 C11 175.0(8) . . . . ? C9 C8 C16 C11 -1.3(7) . . . . ? C5 C4 C17 F1 133.0(7) . . . . ? C3 C4 C17 F1 -50.9(8) . . . . ? C5 C4 C17 F2 -105.8(7) . . . . ? C3 C4 C17 F2 70.2(8) . . . . ? C5 C4 C17 F3 13.8(9) . . . . ? C3 C4 C17 F3 -170.2(6) . . . . ? C14 C13 C18 F6 -5.3(9) . . . . ? C12 C13 C18 F6 175.9(5) . . . . ? C14 C13 C18 F5 -128.5(7) . . . . ? C12 C13 C18 F5 52.7(8) . . . . ? C14 C13 C18 F4 113.9(7) . . . . ? C12 C13 C18 F4 -64.9(8) . . . . ? C8 C7 C19 C24 -39.7(10) . . . . ? C6 C7 C19 C24 137.4(7) . . . . ? C8 C7 C19 C20 138.6(7) . . . . ? C6 C7 C19 C20 -44.2(9) . . . . ? C24 C19 C20 C21 3.2(9) . . . . ? C7 C19 C20 C21 -175.1(6) . . . . ? C19 C20 C21 C22 -1.5(10) . . . . ? C20 C21 C22 C23 -0.7(10) . . . . ? C20 C21 C22 C25 177.4(6) . . . . ? C21 C22 C23 C24 1.1(10) . . . . ? C25 C22 C23 C24 -177.0(6) . . . . ? C22 C23 C24 C19 0.7(10) . . . . ? C20 C19 C24 C23 -2.9(10) . . . . ? C7 C19 C24 C23 175.5(6) . . . . ? C23 C22 C25 F8 -157.6(6) . . . . ? C21 C22 C25 F8 24.3(9) . . . . ? C23 C22 C25 F9 80.1(8) . . . . ? C21 C22 C25 F9 -98.0(7) . . . . ? C23 C22 C25 F7 -36.2(8) . . . . ? C21 C22 C25 F7 145.6(6) . . . . ? C9 C10 C26 C27 46.0(11) . . . . ? C11 C10 C26 C27 -136.2(7) . . . . ? C9 C10 C26 C31 -133.0(7) . . . . ? C11 C10 C26 C31 44.8(9) . . . . ? C31 C26 C27 C28 -1.7(10) . . . . ? C10 C26 C27 C28 179.2(6) . . . . ? C26 C27 C28 C29 0.0(10) . . . . ? C27 C28 C29 C30 1.5(10) . . . . ? C27 C28 C29 C32 -176.2(6) . . . . ? C28 C29 C30 C31 -1.3(10) . . . . ? C32 C29 C30 C31 176.4(6) . . . . ? C29 C30 C31 C26 -0.5(10) . . . . ? C27 C26 C31 C30 2.0(9) . . . . ? C10 C26 C31 C30 -179.0(6) . . . . ? C30 C29 C32 F10 145.2(6) . . . . ? C28 C29 C32 F10 -37.1(8) . . . . ? C30 C29 C32 F12 -94.2(7) . . . . ? C28 C29 C32 F12 83.5(8) . . . . ? C30 C29 C32 F11 25.6(9) . . . . ? C28 C29 C32 F11 -156.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.773 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.133 data_2d _database_code_depnum_ccdc_archive 'CCDC 917509' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H25 O4' _chemical_formula_weight 473.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.463(8) _cell_length_b 15.645(9) _cell_length_c 17.602(10) _cell_angle_alpha 107.771(10) _cell_angle_beta 98.2863(12) _cell_angle_gamma 105.005(10) _cell_volume 3554(3) _cell_formula_units_Z 6 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6351 _cell_measurement_theta_min 3.0060 _cell_measurement_theta_max 25.3884 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1494 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23908 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.1380 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 12266 _reflns_number_gt 6066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1495P)^2^+5.2567P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12266 _refine_ls_number_parameters 984 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1944 _refine_ls_R_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.3452 _refine_ls_wR_factor_gt 0.2795 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0986(4) 0.0672(4) 0.6934(4) 0.0266(13) Uani 1 1 d . . . C2 C 0.0947(4) 0.0929(4) 0.6190(4) 0.0283(13) Uani 1 1 d . . . C3 C 0.1458(4) 0.0442(4) 0.5669(3) 0.0233(12) Uani 1 1 d . . . C4 C 0.1839(4) -0.0109(4) 0.6089(3) 0.0281(13) Uani 1 1 d . . . C5 C 0.2394(4) -0.0714(4) 0.6023(4) 0.0266(13) Uani 1 1 d . . . C6 C 0.2458(4) -0.0953(4) 0.6770(3) 0.0266(13) Uani 1 1 d . . . C7 C 0.1925(4) -0.0492(4) 0.7288(4) 0.0285(13) Uani 1 1 d . . . C8 C 0.1540(4) 0.0065(4) 0.6869(3) 0.0269(13) Uani 1 1 d . . . C9 C 0.0529(4) 0.1545(4) 0.5963(3) 0.0263(13) Uani 1 1 d . . . H1 H 0.0186 0.1874 0.6307 0.032 Uiso 1 1 calc R . . C10 C 0.0616(4) 0.1679(4) 0.5221(3) 0.0274(13) Uani 1 1 d . . . H2 H 0.0334 0.2101 0.5061 0.033 Uiso 1 1 calc R . . C11 C 0.1117(4) 0.1194(4) 0.4717(3) 0.0265(13) Uani 1 1 d . . . C12 C 0.1552(4) 0.0574(4) 0.4945(4) 0.0288(13) Uani 1 1 d . . . H3 H 0.1904 0.0254 0.4606 0.035 Uiso 1 1 calc R . . O1 O 0.1233(3) 0.1281(3) 0.3981(2) 0.0355(10) Uani 1 1 d . . . C13 C 0.0749(5) 0.1845(5) 0.3686(4) 0.0385(16) Uani 1 1 d . . . H4 H 0.0043 0.1616 0.3661 0.058 Uiso 1 1 calc R . . H5 H 0.0839 0.1798 0.3135 0.058 Uiso 1 1 calc R . . H6 H 0.1031 0.2507 0.4059 0.058 Uiso 1 1 calc R . . C14 C 0.2912(4) -0.1541(4) 0.7012(4) 0.0283(13) Uani 1 1 d . . . H7 H 0.3272 -0.1851 0.6675 0.034 Uiso 1 1 calc R . . C15 C 0.2836(4) -0.1672(4) 0.7756(3) 0.0258(13) Uani 1 1 d . . . H8 H 0.3140 -0.2077 0.7924 0.031 Uiso 1 1 calc R . . C16 C 0.2312(4) -0.1209(4) 0.8249(3) 0.0273(13) Uani 1 1 d . . . C17 C 0.1851(4) -0.0613(4) 0.8017(3) 0.0262(13) Uani 1 1 d . . . H9 H 0.1495 -0.0301 0.8357 0.031 Uiso 1 1 calc R . . O2 O 0.2191(3) -0.1296(3) 0.8987(2) 0.0340(10) Uani 1 1 d . . . C18 C 0.2662(4) -0.1875(4) 0.9269(4) 0.0350(15) Uani 1 1 d . . . H10 H 0.2384 -0.2531 0.8881 0.052 Uiso 1 1 calc R . . H11 H 0.2554 -0.1850 0.9811 0.052 Uiso 1 1 calc R . . H12 H 0.3371 -0.1643 0.9309 0.052 Uiso 1 1 calc R . . C19 C 0.0497(4) 0.0979(4) 0.7595(4) 0.0281(13) Uani 1 1 d . . . C20 C -0.0478(4) 0.0938(4) 0.7392(4) 0.0284(13) Uani 1 1 d . . . H13 H -0.0807 0.0759 0.6832 0.034 Uiso 1 1 calc R . . C21 C -0.0981(4) 0.1160(4) 0.8014(4) 0.0329(14) Uani 1 1 d . . . C22 C -0.0498(5) 0.1435(4) 0.8834(4) 0.0405(17) Uani 1 1 d . . . H14 H -0.0836 0.1578 0.9256 0.049 Uiso 1 1 calc R . . C23 C 0.0484(5) 0.1495(4) 0.9024(4) 0.0391(16) Uani 1 1 d . . . H15 H 0.0819 0.1694 0.9585 0.047 Uiso 1 1 calc R . . C24 C 0.0993(5) 0.1279(4) 0.8429(4) 0.0324(14) Uani 1 1 d . . . H16 H 0.1668 0.1329 0.8577 0.039 Uiso 1 1 calc R . . O3 O -0.1959(3) 0.1070(3) 0.7732(3) 0.0464(12) Uani 1 1 d . . . C25 C -0.2517(5) 0.1256(5) 0.8320(5) 0.057(2) Uani 1 1 d . . . H17 H -0.2616 0.0762 0.8562 0.086 Uiso 1 1 calc R . . H18 H -0.3158 0.1260 0.8054 0.086 Uiso 1 1 calc R . . H19 H -0.2163 0.1875 0.8753 0.086 Uiso 1 1 calc R . . C26 C 0.2847(5) -0.1054(4) 0.5341(4) 0.0316(14) Uani 1 1 d . . . C27 C 0.3831(4) -0.1023(4) 0.5498(4) 0.0329(14) Uani 1 1 d . . . H20 H 0.4220 -0.0777 0.6046 0.040 Uiso 1 1 calc R . . C28 C 0.4232(5) -0.1353(4) 0.4844(4) 0.0355(15) Uani 1 1 d . . . C29 C 0.3662(5) -0.1740(5) 0.4037(4) 0.0433(17) Uani 1 1 d . . . H21 H 0.3937 -0.1989 0.3594 0.052 Uiso 1 1 calc R . . C30 C 0.2687(5) -0.1758(4) 0.3890(4) 0.0398(16) Uani 1 1 d . . . H22 H 0.2301 -0.1997 0.3340 0.048 Uiso 1 1 calc R . . C31 C 0.2274(5) -0.1429(4) 0.4536(4) 0.0369(15) Uani 1 1 d . . . H23 H 0.1601 -0.1459 0.4431 0.044 Uiso 1 1 calc R . . O4 O 0.5186(4) -0.1368(4) 0.4929(3) 0.0548(14) Uani 1 1 d . . . C32 C 0.5813(5) -0.0930(6) 0.5730(5) 0.057(2) Uani 1 1 d . . . H24 H 0.5885 -0.0254 0.5935 0.085 Uiso 1 1 calc R . . H25 H 0.6462 -0.1007 0.5714 0.085 Uiso 1 1 calc R . . H26 H 0.5527 -0.1226 0.6096 0.085 Uiso 1 1 calc R . . C33 C 0.4233(4) 0.0666(4) 1.0340(4) 0.0324(14) Uani 1 1 d . . . C34 C 0.4229(4) 0.0861(4) 0.9580(4) 0.0287(13) Uani 1 1 d . . . C35 C 0.4799(4) 0.0381(4) 0.9120(4) 0.0318(14) Uani 1 1 d . . . C36 C 0.5181(4) -0.0102(4) 0.9626(4) 0.0331(14) Uani 1 1 d . . . C37 C 0.3793(4) 0.1426(4) 0.9271(4) 0.0352(15) Uani 1 1 d . . . H27 H 0.3423 0.1760 0.9576 0.042 Uiso 1 1 calc R . . C38 C 0.3902(4) 0.1500(4) 0.8513(4) 0.0293(13) Uani 1 1 d . . . H28 H 0.3611 0.1888 0.8306 0.035 Uiso 1 1 calc R . . C39 C 0.4435(4) 0.1005(4) 0.8065(4) 0.0317(14) Uani 1 1 d . . . C40 C 0.4897(4) 0.0454(4) 0.8381(4) 0.0326(14) Uani 1 1 d . . . H29 H 0.5278 0.0133 0.8079 0.039 Uiso 1 1 calc R . . O5 O 0.4569(3) 0.1008(3) 0.7319(3) 0.0377(10) Uani 1 1 d . . . C41 C 0.4171(5) 0.1605(5) 0.6992(4) 0.0428(17) Uani 1 1 d . . . H30 H 0.3461 0.1434 0.6956 0.064 Uiso 1 1 calc R . . H31 H 0.4286 0.1522 0.6443 0.064 Uiso 1 1 calc R . . H32 H 0.4495 0.2268 0.7354 0.064 Uiso 1 1 calc R . . C42 C 0.3630(4) 0.0945(4) 1.0915(4) 0.0329(14) Uani 1 1 d . . . C43 C 0.2630(4) 0.0784(4) 1.0605(4) 0.0294(13) Uani 1 1 d . . . H33 H 0.2368 0.0540 1.0026 0.035 Uiso 1 1 calc R . . C44 C 0.2017(5) 0.0972(4) 1.1115(4) 0.0357(15) Uani 1 1 d . . . C45 C 0.2377(5) 0.1316(4) 1.1962(4) 0.0355(15) Uani 1 1 d . . . H34 H 0.1949 0.1418 1.2318 0.043 Uiso 1 1 calc R . . C46 C 0.3376(5) 0.1509(4) 1.2277(4) 0.0428(17) Uani 1 1 d . . . H35 H 0.3634 0.1780 1.2856 0.051 Uiso 1 1 calc R . . C47 C 0.4014(4) 0.1319(4) 1.1772(4) 0.0329(14) Uani 1 1 d . . . H36 H 0.4691 0.1438 1.2002 0.039 Uiso 1 1 calc R . . O6 O 0.1053(3) 0.0768(3) 1.0733(3) 0.0395(11) Uani 1 1 d . . . C48 C 0.0381(5) 0.0941(5) 1.1227(4) 0.0452(17) Uani 1 1 d . . . H37 H 0.0415 0.0622 1.1625 0.068 Uiso 1 1 calc R . . H38 H -0.0290 0.0697 1.0876 0.068 Uiso 1 1 calc R . . H39 H 0.0553 0.1625 1.1521 0.068 Uiso 1 1 calc R . . C49 C 0.6200(4) 0.5679(4) 1.0027(4) 0.0328(14) Uani 1 1 d . . . C50 C 0.5239(4) 0.5087(4) 0.9683(4) 0.0309(14) Uani 1 1 d . . . C51 C 0.6356(4) 0.5931(4) 1.0914(4) 0.0337(15) Uani 1 1 d . . . C52 C 0.7165(4) 0.6532(4) 1.1558(4) 0.0308(14) Uani 1 1 d . . . H40 H 0.7756 0.6840 1.1442 0.037 Uiso 1 1 calc R . . C53 C 0.2881(4) 0.3315(4) 0.7637(4) 0.0347(15) Uani 1 1 d . . . H41 H 0.2318 0.2909 0.7206 0.042 Uiso 1 1 calc R . . C54 C 0.3728(5) 0.3740(4) 0.7448(4) 0.0354(15) Uani 1 1 d . . . C55 C 0.4582(5) 0.4350(4) 0.8092(4) 0.0392(16) Uani 1 1 d . . . H42 H 0.5176 0.4641 0.7970 0.047 Uiso 1 1 calc R . . C56 C 0.4521(4) 0.4504(4) 0.8890(4) 0.0330(14) Uani 1 1 d . . . O7 O 0.3874(3) 0.3632(3) 0.6685(3) 0.0430(11) Uani 1 1 d . . . C57 C 0.3037(5) 0.3044(5) 0.6018(4) 0.056(2) Uani 1 1 d . . . H43 H 0.2821 0.2408 0.6043 0.084 Uiso 1 1 calc R . . H44 H 0.3218 0.3005 0.5496 0.084 Uiso 1 1 calc R . . H45 H 0.2500 0.3316 0.6059 0.084 Uiso 1 1 calc R . . C58 C 0.6926(4) 0.6001(4) 0.9581(4) 0.0333(15) Uani 1 1 d . . . C59 C 0.7887(4) 0.5998(4) 0.9803(4) 0.0313(14) Uani 1 1 d . . . H46 H 0.8078 0.5810 1.0250 0.038 Uiso 1 1 calc R . . C60 C 0.8573(4) 0.6271(4) 0.9366(4) 0.0322(14) Uani 1 1 d . . . C61 C 0.8307(5) 0.6548(4) 0.8720(4) 0.0410(16) Uani 1 1 d . . . H47 H 0.8770 0.6725 0.8419 0.049 Uiso 1 1 calc R . . C62 C 0.7342(5) 0.6564(4) 0.8512(4) 0.0447(17) Uani 1 1 d . . . H48 H 0.7149 0.6758 0.8070 0.054 Uiso 1 1 calc R . . C63 C 0.6674(5) 0.6298(4) 0.8946(4) 0.0377(16) Uani 1 1 d . . . H49 H 0.6024 0.6321 0.8803 0.045 Uiso 1 1 calc R . . O8 O 0.9492(3) 0.6243(3) 0.9649(3) 0.0435(11) Uani 1 1 d . . . C64 C 1.0223(5) 0.6483(6) 0.9224(4) 0.055(2) Uani 1 1 d . . . H50 H 1.0025 0.6022 0.8660 0.083 Uiso 1 1 calc R . . H51 H 1.0853 0.6473 0.9507 0.083 Uiso 1 1 calc R . . H52 H 1.0296 0.7118 0.9211 0.083 Uiso 1 1 calc R . . C65 C 0.0508(4) 0.4372(4) 0.6900(4) 0.0303(14) Uani 1 1 d . . . C66 C 0.0304(4) 0.4146(4) 0.6005(3) 0.0248(13) Uani 1 1 d . . . C67 C 0.1172(4) 0.4557(4) 0.5789(4) 0.0298(14) Uani 1 1 d . . . C68 C 0.1933(4) 0.5061(4) 0.6565(3) 0.0284(13) Uani 1 1 d . . . C69 C 0.2909(4) 0.5629(4) 0.6883(4) 0.0283(13) Uani 1 1 d . . . C70 C 0.3099(4) 0.5869(4) 0.7781(4) 0.0291(13) Uani 1 1 d . . . C71 C 0.2230(4) 0.5428(4) 0.7991(4) 0.0271(13) Uani 1 1 d . . . C72 C 0.1485(4) 0.4897(4) 0.7219(4) 0.0276(13) Uani 1 1 d . . . C73 C -0.0544(4) 0.3606(4) 0.5390(3) 0.0302(14) Uani 1 1 d . . . H53 H -0.1130 0.3322 0.5526 0.036 Uiso 1 1 calc R . . C74 C -0.0539(4) 0.3476(4) 0.4572(4) 0.0270(13) Uani 1 1 d . . . H54 H -0.1117 0.3091 0.4149 0.032 Uiso 1 1 calc R . . C75 C 0.0300(5) 0.3906(4) 0.4378(4) 0.0325(14) Uani 1 1 d . . . C76 C 0.1186(4) 0.4460(4) 0.4992(3) 0.0260(13) Uani 1 1 d . . . H55 H 0.1767 0.4752 0.4855 0.031 Uiso 1 1 calc R . . O9 O 0.0395(3) 0.3836(3) 0.3586(3) 0.0350(10) Uani 1 1 d . . . C77 C -0.0453(4) 0.3270(5) 0.2937(4) 0.0380(15) Uani 1 1 d . . . H56 H -0.0661 0.2625 0.2944 0.057 Uiso 1 1 calc R . . H57 H -0.0297 0.3252 0.2410 0.057 Uiso 1 1 calc R . . H58 H -0.0988 0.3542 0.3009 0.057 Uiso 1 1 calc R . . C78 C 0.2218(4) 0.5566(4) 0.8801(4) 0.0279(13) Uani 1 1 d . . . H59 H 0.1644 0.5261 0.8940 0.034 Uiso 1 1 calc R . . C79 C 0.3070(4) 0.6168(4) 0.9415(3) 0.0255(13) Uani 1 1 d . . . C80 C 0.3921(4) 0.6596(4) 0.9214(4) 0.0315(14) Uani 1 1 d . . . H60 H 0.4498 0.6981 0.9638 0.038 Uiso 1 1 calc R . . C81 C 0.3934(4) 0.6465(4) 0.8399(4) 0.0302(14) Uani 1 1 d . . . H61 H 0.4508 0.6780 0.8265 0.036 Uiso 1 1 calc R . . O10 O 0.2983(3) 0.6265(3) 1.0200(3) 0.0366(10) Uani 1 1 d . . . C82 C 0.3833(5) 0.6874(5) 1.0851(4) 0.0430(17) Uani 1 1 d . . . C83 C -0.0213(4) 0.4103(4) 0.7374(4) 0.0305(14) Uani 1 1 d . . . C84 C -0.1144(4) 0.4226(4) 0.7213(4) 0.0331(14) Uani 1 1 d . . . H62 H -0.1328 0.4437 0.6779 0.040 Uiso 1 1 calc R . . C85 C -0.1783(4) 0.4035(4) 0.7694(4) 0.0368(15) Uani 1 1 d . . . C86 C -0.1504(5) 0.3754(4) 0.8349(4) 0.0412(16) Uani 1 1 d . . . H63 H -0.1935 0.3657 0.8696 0.049 Uiso 1 1 calc R . . C87 C -0.0615(5) 0.3619(5) 0.8487(4) 0.0423(16) Uani 1 1 d . . . H64 H -0.0432 0.3409 0.8921 0.051 Uiso 1 1 calc R . . C88 C 0.0032(5) 0.3786(4) 0.7994(4) 0.0357(15) Uani 1 1 d . . . H65 H 0.0649 0.3679 0.8090 0.043 Uiso 1 1 calc R . . O11 O -0.2718(3) 0.4112(3) 0.7588(3) 0.0498(13) Uani 1 1 d . . . C89 C -0.3029(6) 0.4365(6) 0.6923(4) 0.057(2) Uani 1 1 d . . . H66 H -0.2615 0.5008 0.7010 0.086 Uiso 1 1 calc R . . H67 H -0.3718 0.4347 0.6877 0.086 Uiso 1 1 calc R . . H68 H -0.2973 0.3920 0.6416 0.086 Uiso 1 1 calc R . . C90 C 0.3636(4) 0.5922(4) 0.6419(4) 0.0315(14) Uani 1 1 d . . . C91 C 0.4563(4) 0.5859(4) 0.6602(4) 0.0300(14) Uani 1 1 d . . . H69 H 0.4739 0.5641 0.7033 0.036 Uiso 1 1 calc R . . C92 C 0.5257(4) 0.6113(4) 0.6163(4) 0.0361(15) Uani 1 1 d . . . C93 C 0.5006(5) 0.6462(4) 0.5552(4) 0.0378(15) Uani 1 1 d . . . H70 H 0.5468 0.6641 0.5251 0.045 Uiso 1 1 calc R . . C94 C 0.4069(5) 0.6547(4) 0.5389(4) 0.0394(16) Uani 1 1 d . . . H71 H 0.3897 0.6792 0.4976 0.047 Uiso 1 1 calc R . . C95 C 0.3383(4) 0.6281(4) 0.5818(4) 0.0318(14) Uani 1 1 d . . . H72 H 0.2747 0.6342 0.5701 0.038 Uiso 1 1 calc R . . O12 O 0.6152(3) 0.6002(3) 0.6387(3) 0.0424(11) Uani 1 1 d . . . C96 C 0.6873(5) 0.6244(5) 0.5946(4) 0.0513(19) Uani 1 1 d . . . H73 H 0.6621 0.5841 0.5364 0.077 Uiso 1 1 calc R . . H74 H 0.7481 0.6145 0.6170 0.077 Uiso 1 1 calc R . . H75 H 0.7011 0.6910 0.6003 0.077 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(3) 0.021(3) 0.031(3) 0.010(3) 0.004(2) 0.005(2) C2 0.031(3) 0.025(3) 0.028(3) 0.007(3) 0.005(3) 0.012(3) C3 0.022(3) 0.016(3) 0.029(3) 0.006(2) 0.005(2) 0.005(2) C4 0.028(3) 0.029(3) 0.026(3) 0.007(3) 0.004(2) 0.011(3) C5 0.025(3) 0.022(3) 0.031(3) 0.009(3) 0.011(2) 0.004(2) C6 0.027(3) 0.023(3) 0.024(3) 0.004(2) 0.003(2) 0.007(2) C7 0.029(3) 0.028(3) 0.030(3) 0.011(3) 0.005(3) 0.013(3) C8 0.022(3) 0.018(3) 0.029(3) 0.002(2) 0.002(2) -0.003(2) C9 0.021(3) 0.028(3) 0.029(3) 0.006(3) 0.008(2) 0.009(2) C10 0.030(3) 0.017(3) 0.029(3) 0.002(2) -0.002(3) 0.011(2) C11 0.029(3) 0.025(3) 0.024(3) 0.006(3) 0.008(2) 0.008(2) C12 0.032(3) 0.020(3) 0.031(3) 0.004(3) 0.004(3) 0.009(2) O1 0.047(3) 0.039(2) 0.028(2) 0.012(2) 0.012(2) 0.024(2) C13 0.049(4) 0.045(4) 0.032(4) 0.016(3) 0.012(3) 0.029(3) C14 0.029(3) 0.020(3) 0.031(3) 0.005(3) 0.004(3) 0.007(2) C15 0.024(3) 0.022(3) 0.030(3) 0.011(3) 0.001(2) 0.006(2) C16 0.028(3) 0.025(3) 0.027(3) 0.013(3) 0.000(2) 0.004(2) C17 0.015(3) 0.026(3) 0.032(3) 0.005(3) 0.007(2) 0.003(2) O2 0.041(2) 0.033(2) 0.033(2) 0.017(2) 0.0133(19) 0.0142(19) C18 0.039(4) 0.030(3) 0.035(4) 0.013(3) 0.001(3) 0.012(3) C19 0.035(3) 0.020(3) 0.029(3) 0.007(3) 0.013(3) 0.009(2) C20 0.029(3) 0.026(3) 0.029(3) 0.008(3) 0.010(3) 0.008(2) C21 0.034(4) 0.033(3) 0.036(4) 0.017(3) 0.011(3) 0.012(3) C22 0.070(5) 0.027(3) 0.041(4) 0.019(3) 0.026(4) 0.027(3) C23 0.056(4) 0.028(3) 0.027(3) 0.006(3) 0.003(3) 0.013(3) C24 0.044(4) 0.024(3) 0.030(3) 0.005(3) 0.008(3) 0.018(3) O3 0.046(3) 0.054(3) 0.055(3) 0.024(3) 0.029(2) 0.027(2) C25 0.063(5) 0.057(5) 0.074(6) 0.033(4) 0.046(4) 0.031(4) C26 0.048(4) 0.028(3) 0.025(3) 0.008(3) 0.015(3) 0.019(3) C27 0.038(4) 0.041(4) 0.034(4) 0.022(3) 0.015(3) 0.023(3) C28 0.040(4) 0.037(4) 0.047(4) 0.022(3) 0.023(3) 0.026(3) C29 0.067(5) 0.041(4) 0.032(4) 0.014(3) 0.025(3) 0.025(4) C30 0.049(4) 0.038(4) 0.035(4) 0.014(3) 0.013(3) 0.016(3) C31 0.050(4) 0.031(3) 0.031(4) 0.010(3) 0.012(3) 0.015(3) O4 0.053(3) 0.079(4) 0.058(3) 0.037(3) 0.030(3) 0.039(3) C32 0.044(4) 0.066(5) 0.070(6) 0.036(5) 0.019(4) 0.016(4) C33 0.027(3) 0.016(3) 0.043(4) 0.004(3) 0.004(3) 0.001(2) C34 0.023(3) 0.022(3) 0.034(3) 0.006(3) 0.002(3) 0.004(2) C35 0.021(3) 0.020(3) 0.046(4) 0.005(3) 0.006(3) 0.003(2) C36 0.023(3) 0.025(3) 0.045(4) 0.011(3) 0.003(3) 0.004(2) C37 0.021(3) 0.029(3) 0.049(4) 0.009(3) 0.002(3) 0.008(3) C38 0.028(3) 0.021(3) 0.032(3) 0.004(3) 0.005(3) 0.005(2) C39 0.022(3) 0.029(3) 0.033(4) 0.001(3) 0.004(3) 0.005(3) C40 0.021(3) 0.029(3) 0.039(4) -0.001(3) 0.008(3) 0.008(3) O5 0.039(3) 0.039(3) 0.037(3) 0.013(2) 0.014(2) 0.014(2) C41 0.041(4) 0.045(4) 0.044(4) 0.021(3) 0.015(3) 0.009(3) C42 0.038(4) 0.026(3) 0.032(4) 0.004(3) 0.009(3) 0.014(3) C43 0.032(3) 0.031(3) 0.025(3) 0.005(3) 0.007(3) 0.015(3) C44 0.044(4) 0.032(3) 0.029(3) 0.008(3) 0.003(3) 0.016(3) C45 0.049(4) 0.042(4) 0.028(3) 0.015(3) 0.018(3) 0.026(3) C46 0.067(5) 0.035(4) 0.030(4) 0.009(3) 0.014(3) 0.023(3) C47 0.035(3) 0.029(3) 0.032(4) 0.007(3) 0.000(3) 0.015(3) O6 0.034(2) 0.046(3) 0.037(3) 0.012(2) 0.010(2) 0.014(2) C48 0.060(5) 0.043(4) 0.050(4) 0.021(4) 0.029(4) 0.030(4) C49 0.036(4) 0.016(3) 0.043(4) 0.009(3) 0.003(3) 0.008(3) C50 0.029(3) 0.017(3) 0.040(4) 0.006(3) 0.003(3) 0.005(2) C51 0.029(3) 0.020(3) 0.044(4) 0.000(3) 0.001(3) 0.013(3) C52 0.028(3) 0.021(3) 0.039(4) 0.008(3) 0.002(3) 0.008(2) C53 0.034(4) 0.026(3) 0.032(4) 0.001(3) -0.006(3) 0.009(3) C54 0.038(4) 0.022(3) 0.041(4) 0.006(3) 0.006(3) 0.009(3) C55 0.035(4) 0.028(3) 0.051(4) 0.014(3) 0.000(3) 0.009(3) C56 0.030(3) 0.023(3) 0.038(4) 0.005(3) 0.000(3) 0.008(3) O7 0.043(3) 0.033(2) 0.035(3) 0.007(2) -0.004(2) -0.004(2) C57 0.060(5) 0.045(4) 0.044(4) 0.014(4) -0.001(4) -0.005(4) C58 0.025(3) 0.022(3) 0.042(4) 0.008(3) -0.002(3) -0.001(2) C59 0.028(3) 0.030(3) 0.026(3) 0.004(3) -0.002(3) 0.006(3) C60 0.025(3) 0.025(3) 0.040(4) 0.006(3) 0.004(3) 0.006(2) C61 0.043(4) 0.035(4) 0.036(4) 0.012(3) 0.006(3) 0.002(3) C62 0.052(4) 0.028(3) 0.042(4) 0.012(3) 0.001(3) -0.001(3) C63 0.037(4) 0.023(3) 0.042(4) 0.009(3) -0.008(3) 0.003(3) O8 0.036(3) 0.053(3) 0.037(3) 0.011(2) 0.008(2) 0.013(2) C64 0.052(5) 0.067(5) 0.040(4) 0.010(4) 0.015(4) 0.016(4) C65 0.033(3) 0.022(3) 0.035(4) 0.008(3) 0.008(3) 0.010(3) C66 0.026(3) 0.019(3) 0.032(3) 0.011(3) 0.005(2) 0.009(2) C67 0.036(3) 0.023(3) 0.029(3) 0.009(3) 0.006(3) 0.009(3) C68 0.034(3) 0.023(3) 0.024(3) 0.003(3) 0.006(3) 0.010(3) C69 0.028(3) 0.028(3) 0.032(3) 0.011(3) 0.009(3) 0.014(3) C70 0.031(3) 0.023(3) 0.030(3) 0.007(3) 0.008(3) 0.007(3) C71 0.026(3) 0.015(3) 0.036(3) 0.008(3) 0.002(3) 0.005(2) C72 0.027(3) 0.023(3) 0.035(3) 0.010(3) 0.006(3) 0.011(2) C73 0.025(3) 0.037(3) 0.027(3) 0.007(3) 0.009(3) 0.011(3) C74 0.024(3) 0.017(3) 0.035(3) 0.008(3) -0.002(3) 0.004(2) C75 0.048(4) 0.029(3) 0.027(3) 0.009(3) 0.011(3) 0.021(3) C76 0.025(3) 0.022(3) 0.028(3) 0.003(2) 0.007(2) 0.009(2) O9 0.036(2) 0.028(2) 0.036(3) 0.0068(19) 0.0052(19) 0.0090(18) C77 0.041(4) 0.042(4) 0.029(3) 0.007(3) 0.008(3) 0.017(3) C78 0.031(3) 0.020(3) 0.033(3) 0.010(3) 0.006(3) 0.009(2) C79 0.027(3) 0.026(3) 0.025(3) 0.010(3) 0.004(2) 0.010(2) C80 0.033(3) 0.023(3) 0.034(4) 0.006(3) 0.002(3) 0.010(3) C81 0.025(3) 0.031(3) 0.033(3) 0.009(3) 0.006(3) 0.011(3) O10 0.034(2) 0.039(3) 0.033(2) 0.010(2) 0.0058(19) 0.0091(19) C82 0.036(4) 0.046(4) 0.027(4) 0.001(3) -0.005(3) 0.002(3) C83 0.030(3) 0.027(3) 0.030(3) 0.006(3) 0.006(3) 0.006(3) C84 0.039(4) 0.029(3) 0.026(3) 0.005(3) 0.005(3) 0.008(3) C85 0.020(3) 0.037(4) 0.041(4) 0.002(3) 0.003(3) 0.007(3) C86 0.044(4) 0.039(4) 0.038(4) 0.015(3) 0.010(3) 0.008(3) C87 0.048(4) 0.039(4) 0.038(4) 0.016(3) 0.006(3) 0.010(3) C88 0.032(3) 0.033(3) 0.042(4) 0.013(3) 0.006(3) 0.013(3) O11 0.042(3) 0.061(3) 0.047(3) 0.017(3) 0.011(2) 0.018(2) C89 0.064(5) 0.065(5) 0.046(5) 0.023(4) 0.005(4) 0.027(4) C90 0.035(4) 0.020(3) 0.035(4) 0.005(3) 0.003(3) 0.009(3) C91 0.031(3) 0.028(3) 0.030(3) 0.007(3) 0.010(3) 0.009(3) C92 0.034(4) 0.039(4) 0.033(4) 0.011(3) 0.010(3) 0.009(3) C93 0.039(4) 0.035(4) 0.036(4) 0.012(3) 0.015(3) 0.003(3) C94 0.048(4) 0.034(4) 0.031(4) 0.012(3) 0.004(3) 0.008(3) C95 0.031(3) 0.025(3) 0.030(3) 0.004(3) -0.004(3) 0.007(3) O12 0.025(2) 0.060(3) 0.049(3) 0.024(2) 0.018(2) 0.017(2) C96 0.041(4) 0.072(5) 0.044(4) 0.018(4) 0.022(3) 0.021(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C8 1.383(7) . ? C1 C19 1.469(8) . ? C1 C2 1.480(8) . ? C2 C9 1.387(7) . ? C2 C3 1.425(8) . ? C3 C12 1.371(8) . ? C3 C4 1.454(7) . ? C4 C5 1.380(7) . ? C4 C8 1.465(8) . ? C5 C6 1.469(8) . ? C5 C26 1.474(8) . ? C6 C14 1.389(7) . ? C6 C7 1.427(8) . ? C7 C17 1.368(8) . ? C7 C8 1.462(7) . ? C9 C10 1.403(8) . ? C9 H1 0.9500 . ? C10 C11 1.395(8) . ? C10 H2 0.9500 . ? C11 O1 1.372(7) . ? C11 C12 1.407(7) . ? C12 H3 0.9500 . ? O1 C13 1.425(6) . ? C13 H4 0.9800 . ? C13 H5 0.9800 . ? C13 H6 0.9800 . ? C14 C15 1.402(8) . ? C14 H7 0.9500 . ? C15 C16 1.394(8) . ? C15 H8 0.9500 . ? C16 O2 1.378(7) . ? C16 C17 1.398(7) . ? C17 H9 0.9500 . ? O2 C18 1.424(6) . ? C18 H10 0.9800 . ? C18 H11 0.9800 . ? C18 H12 0.9800 . ? C19 C20 1.384(8) . ? C19 C24 1.411(8) . ? C20 C21 1.406(8) . ? C20 H13 0.9500 . ? C21 O3 1.385(7) . ? C21 C22 1.391(9) . ? C22 C23 1.383(9) . ? C22 H14 0.9500 . ? C23 C24 1.374(8) . ? C23 H15 0.9500 . ? C24 H16 0.9500 . ? O3 C25 1.409(7) . ? C25 H17 0.9800 . ? C25 H18 0.9800 . ? C25 H19 0.9800 . ? C26 C31 1.394(8) . ? C26 C27 1.395(8) . ? C27 C28 1.383(8) . ? C27 H20 0.9500 . ? C28 O4 1.373(7) . ? C28 C29 1.394(9) . ? C29 C30 1.388(9) . ? C29 H21 0.9500 . ? C30 C31 1.383(8) . ? C30 H22 0.9500 . ? C31 H23 0.9500 . ? O4 C32 1.414(9) . ? C32 H24 0.9800 . ? C32 H25 0.9800 . ? C32 H26 0.9800 . ? C33 C36 1.380(8) 2_657 ? C33 C34 1.460(8) . ? C33 C42 1.467(8) . ? C34 C37 1.399(8) . ? C34 C35 1.429(8) . ? C35 C40 1.363(9) . ? C35 C36 1.468(8) . ? C36 C33 1.380(8) 2_657 ? C36 C36 1.462(12) 2_657 ? C37 C38 1.401(8) . ? C37 H27 0.9500 . ? C38 C39 1.389(8) . ? C38 H28 0.9500 . ? C39 O5 1.356(7) . ? C39 C40 1.407(8) . ? C40 H29 0.9500 . ? O5 C41 1.430(7) . ? C41 H30 0.9800 . ? C41 H31 0.9800 . ? C41 H32 0.9800 . ? C42 C43 1.398(8) . ? C42 C47 1.406(8) . ? C43 C44 1.372(8) . ? C43 H33 0.9500 . ? C44 O6 1.366(7) . ? C44 C45 1.386(8) . ? C45 C46 1.389(9) . ? C45 H34 0.9500 . ? C46 C47 1.396(9) . ? C46 H35 0.9500 . ? C47 H36 0.9500 . ? O6 C48 1.418(7) . ? C48 H37 0.9800 . ? C48 H38 0.9800 . ? C48 H39 0.9800 . ? C49 C50 1.380(8) . ? C49 C51 1.456(9) . ? C49 C58 1.474(9) . ? C50 C50 1.453(12) 2_667 ? C50 C56 1.474(8) . ? C51 C52 1.391(8) . ? C51 C56 1.420(9) 2_667 ? C52 C53 1.378(8) 2_667 ? C52 H40 0.9500 . ? C53 C54 1.373(9) . ? C53 C52 1.378(8) 2_667 ? C53 H41 0.9500 . ? C54 O7 1.355(7) . ? C54 C55 1.431(8) . ? C55 C56 1.371(9) . ? C55 H42 0.9500 . ? C56 C51 1.420(9) 2_667 ? O7 C57 1.429(7) . ? C57 H43 0.9800 . ? C57 H44 0.9800 . ? C57 H45 0.9800 . ? C58 C63 1.374(8) . ? C58 C59 1.391(8) . ? C59 C60 1.401(8) . ? C59 H46 0.9500 . ? C60 O8 1.367(7) . ? C60 C61 1.374(8) . ? C61 C62 1.399(9) . ? C61 H47 0.9500 . ? C62 C63 1.374(9) . ? C62 H48 0.9500 . ? C63 H49 0.9500 . ? O8 C64 1.418(8) . ? C64 H50 0.9800 . ? C64 H51 0.9800 . ? C64 H52 0.9800 . ? C65 C72 1.369(8) . ? C65 C66 1.472(8) . ? C65 C83 1.483(8) . ? C66 C73 1.382(8) . ? C66 C67 1.416(8) . ? C67 C76 1.368(8) . ? C67 C68 1.468(8) . ? C68 C69 1.384(8) . ? C68 C72 1.455(8) . ? C69 C70 1.475(8) . ? C69 C90 1.485(8) . ? C70 C81 1.390(8) . ? C70 C71 1.425(8) . ? C71 C78 1.379(8) . ? C71 C72 1.457(8) . ? C73 C74 1.393(8) . ? C73 H53 0.9500 . ? C74 C75 1.370(8) . ? C74 H54 0.9500 . ? C75 O9 1.394(7) . ? C75 C76 1.420(8) . ? C76 H55 0.9500 . ? O9 C77 1.418(7) . ? C77 H56 0.9800 . ? C77 H57 0.9800 . ? C77 H58 0.9800 . ? C78 C79 1.403(8) . ? C78 H59 0.9500 . ? C79 O10 1.372(7) . ? C79 C80 1.388(8) . ? C80 C81 1.391(8) . ? C80 H60 0.9500 . ? C81 H61 0.9500 . ? O10 C82 1.433(7) . ? C83 C88 1.368(8) . ? C83 C84 1.410(8) . ? C84 C85 1.379(8) . ? C84 H62 0.9500 . ? C85 O11 1.378(7) . ? C85 C86 1.397(9) . ? C86 C87 1.356(9) . ? C86 H63 0.9500 . ? C87 C88 1.393(9) . ? C87 H64 0.9500 . ? C88 H65 0.9500 . ? O11 C89 1.399(8) . ? C89 H66 0.9800 . ? C89 H67 0.9800 . ? C89 H68 0.9800 . ? C90 C91 1.369(8) . ? C90 C95 1.389(8) . ? C91 C92 1.402(8) . ? C91 H69 0.9500 . ? C92 O12 1.368(7) . ? C92 C93 1.392(8) . ? C93 C94 1.394(9) . ? C93 H70 0.9500 . ? C94 C95 1.386(8) . ? C94 H71 0.9500 . ? C95 H72 0.9500 . ? O12 C96 1.428(7) . ? C96 H73 0.9800 . ? C96 H74 0.9800 . ? C96 H75 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C1 C19 127.0(5) . . ? C8 C1 C2 106.8(5) . . ? C19 C1 C2 126.2(5) . . ? C9 C2 C3 119.7(5) . . ? C9 C2 C1 130.8(5) . . ? C3 C2 C1 109.6(5) . . ? C12 C3 C2 121.3(5) . . ? C12 C3 C4 132.3(5) . . ? C2 C3 C4 106.3(5) . . ? C5 C4 C3 142.5(6) . . ? C5 C4 C8 109.8(5) . . ? C3 C4 C8 107.6(5) . . ? C4 C5 C6 107.0(5) . . ? C4 C5 C26 127.0(5) . . ? C6 C5 C26 126.0(5) . . ? C14 C6 C7 119.1(5) . . ? C14 C6 C5 131.0(5) . . ? C7 C6 C5 109.9(5) . . ? C17 C7 C6 121.7(5) . . ? C17 C7 C8 132.4(5) . . ? C6 C7 C8 105.9(5) . . ? C1 C8 C7 142.9(6) . . ? C1 C8 C4 109.7(5) . . ? C7 C8 C4 107.3(5) . . ? C2 C9 C10 119.3(5) . . ? C2 C9 H1 120.3 . . ? C10 C9 H1 120.3 . . ? C11 C10 C9 120.2(5) . . ? C11 C10 H2 119.9 . . ? C9 C10 H2 119.9 . . ? O1 C11 C10 123.9(5) . . ? O1 C11 C12 115.1(5) . . ? C10 C11 C12 120.9(5) . . ? C3 C12 C11 118.5(5) . . ? C3 C12 H3 120.7 . . ? C11 C12 H3 120.7 . . ? C11 O1 C13 117.8(4) . . ? O1 C13 H4 109.5 . . ? O1 C13 H5 109.5 . . ? H4 C13 H5 109.5 . . ? O1 C13 H6 109.5 . . ? H4 C13 H6 109.5 . . ? H5 C13 H6 109.5 . . ? C6 C14 C15 119.5(5) . . ? C6 C14 H7 120.2 . . ? C15 C14 H7 120.2 . . ? C16 C15 C14 119.9(5) . . ? C16 C15 H8 120.1 . . ? C14 C15 H8 120.1 . . ? O2 C16 C15 124.2(5) . . ? O2 C16 C17 114.3(5) . . ? C15 C16 C17 121.5(5) . . ? C7 C17 C16 118.3(5) . . ? C7 C17 H9 120.9 . . ? C16 C17 H9 120.9 . . ? C16 O2 C18 117.2(5) . . ? O2 C18 H10 109.5 . . ? O2 C18 H11 109.5 . . ? H10 C18 H11 109.5 . . ? O2 C18 H12 109.5 . . ? H10 C18 H12 109.5 . . ? H11 C18 H12 109.5 . . ? C20 C19 C24 119.7(5) . . ? C20 C19 C1 119.1(5) . . ? C24 C19 C1 121.1(5) . . ? C19 C20 C21 120.0(6) . . ? C19 C20 H13 120.0 . . ? C21 C20 H13 120.0 . . ? O3 C21 C22 125.2(6) . . ? O3 C21 C20 114.6(5) . . ? C22 C21 C20 120.2(6) . . ? C23 C22 C21 118.8(6) . . ? C23 C22 H14 120.6 . . ? C21 C22 H14 120.6 . . ? C24 C23 C22 122.2(6) . . ? C24 C23 H15 118.9 . . ? C22 C23 H15 118.9 . . ? C23 C24 C19 119.1(6) . . ? C23 C24 H16 120.5 . . ? C19 C24 H16 120.5 . . ? C21 O3 C25 117.6(6) . . ? O3 C25 H17 109.5 . . ? O3 C25 H18 109.5 . . ? H17 C25 H18 109.5 . . ? O3 C25 H19 109.5 . . ? H17 C25 H19 109.5 . . ? H18 C25 H19 109.5 . . ? C31 C26 C27 120.2(6) . . ? C31 C26 C5 119.2(6) . . ? C27 C26 C5 120.6(5) . . ? C28 C27 C26 119.2(6) . . ? C28 C27 H20 120.4 . . ? C26 C27 H20 120.4 . . ? O4 C28 C27 124.0(6) . . ? O4 C28 C29 114.9(6) . . ? C27 C28 C29 121.0(6) . . ? C30 C29 C28 119.2(6) . . ? C30 C29 H21 120.4 . . ? C28 C29 H21 120.4 . . ? C31 C30 C29 120.5(6) . . ? C31 C30 H22 119.7 . . ? C29 C30 H22 119.7 . . ? C30 C31 C26 119.8(6) . . ? C30 C31 H23 120.1 . . ? C26 C31 H23 120.1 . . ? C28 O4 C32 117.1(5) . . ? O4 C32 H24 109.5 . . ? O4 C32 H25 109.5 . . ? H24 C32 H25 109.5 . . ? O4 C32 H26 109.5 . . ? H24 C32 H26 109.5 . . ? H25 C32 H26 109.5 . . ? C36 C33 C34 108.0(5) 2_657 . ? C36 C33 C42 126.7(6) 2_657 . ? C34 C33 C42 125.0(5) . . ? C37 C34 C35 119.0(6) . . ? C37 C34 C33 131.1(6) . . ? C35 C34 C33 110.0(5) . . ? C40 C35 C34 120.5(5) . . ? C40 C35 C36 134.4(6) . . ? C34 C35 C36 105.0(5) . . ? C33 C36 C36 108.6(6) 2_657 2_657 ? C33 C36 C35 143.0(6) 2_657 . ? C36 C36 C35 108.3(6) 2_657 . ? C34 C37 C38 120.1(6) . . ? C34 C37 H27 120.0 . . ? C38 C37 H27 120.0 . . ? C39 C38 C37 119.9(6) . . ? C39 C38 H28 120.0 . . ? C37 C38 H28 120.0 . . ? O5 C39 C38 124.9(5) . . ? O5 C39 C40 114.8(5) . . ? C38 C39 C40 120.4(6) . . ? C35 C40 C39 120.1(5) . . ? C35 C40 H29 119.9 . . ? C39 C40 H29 119.9 . . ? C39 O5 C41 117.2(5) . . ? O5 C41 H30 109.5 . . ? O5 C41 H31 109.5 . . ? H30 C41 H31 109.5 . . ? O5 C41 H32 109.5 . . ? H30 C41 H32 109.5 . . ? H31 C41 H32 109.5 . . ? C43 C42 C47 118.8(6) . . ? C43 C42 C33 119.1(5) . . ? C47 C42 C33 122.0(5) . . ? C44 C43 C42 121.6(6) . . ? C44 C43 H33 119.2 . . ? C42 C43 H33 119.2 . . ? O6 C44 C43 115.7(5) . . ? O6 C44 C45 123.9(6) . . ? C43 C44 C45 120.4(6) . . ? C44 C45 C46 118.5(6) . . ? C44 C45 H34 120.8 . . ? C46 C45 H34 120.8 . . ? C45 C46 C47 122.2(6) . . ? C45 C46 H35 118.9 . . ? C47 C46 H35 118.9 . . ? C46 C47 C42 118.4(6) . . ? C46 C47 H36 120.8 . . ? C42 C47 H36 120.8 . . ? C44 O6 C48 118.4(5) . . ? O6 C48 H37 109.5 . . ? O6 C48 H38 109.5 . . ? H37 C48 H38 109.5 . . ? O6 C48 H39 109.5 . . ? H37 C48 H39 109.5 . . ? H38 C48 H39 109.5 . . ? C50 C49 C51 106.8(6) . . ? C50 C49 C58 126.5(6) . . ? C51 C49 C58 126.7(5) . . ? C49 C50 C50 110.5(7) . 2_667 ? C49 C50 C56 142.9(6) . . ? C50 C50 C56 106.4(6) 2_667 . ? C52 C51 C56 118.2(6) . 2_667 ? C52 C51 C49 131.6(6) . . ? C56 C51 C49 110.1(5) 2_667 . ? C53 C52 C51 120.7(6) 2_667 . ? C53 C52 H40 119.6 2_667 . ? C51 C52 H40 119.6 . . ? C54 C53 C52 121.1(6) . 2_667 ? C54 C53 H41 119.5 . . ? C52 C53 H41 119.5 2_667 . ? O7 C54 C53 126.7(6) . . ? O7 C54 C55 113.4(6) . . ? C53 C54 C55 119.9(6) . . ? C56 C55 C54 118.4(6) . . ? C56 C55 H42 120.8 . . ? C54 C55 H42 120.8 . . ? C55 C56 C51 121.7(6) . 2_667 ? C55 C56 C50 132.2(6) . . ? C51 C56 C50 106.0(5) 2_667 . ? C54 O7 C57 115.6(5) . . ? O7 C57 H43 109.5 . . ? O7 C57 H44 109.5 . . ? H43 C57 H44 109.5 . . ? O7 C57 H45 109.5 . . ? H43 C57 H45 109.5 . . ? H44 C57 H45 109.5 . . ? C63 C58 C59 119.0(6) . . ? C63 C58 C49 121.6(6) . . ? C59 C58 C49 119.4(6) . . ? C58 C59 C60 119.9(6) . . ? C58 C59 H46 120.1 . . ? C60 C59 H46 120.1 . . ? O8 C60 C61 125.3(6) . . ? O8 C60 C59 114.1(5) . . ? C61 C60 C59 120.6(6) . . ? C60 C61 C62 119.0(6) . . ? C60 C61 H47 120.5 . . ? C62 C61 H47 120.5 . . ? C63 C62 C61 120.1(6) . . ? C63 C62 H48 119.9 . . ? C61 C62 H48 119.9 . . ? C58 C63 C62 121.4(6) . . ? C58 C63 H49 119.3 . . ? C62 C63 H49 119.3 . . ? C60 O8 C64 117.7(5) . . ? O8 C64 H50 109.5 . . ? O8 C64 H51 109.5 . . ? H50 C64 H51 109.5 . . ? O8 C64 H52 109.5 . . ? H50 C64 H52 109.5 . . ? H51 C64 H52 109.5 . . ? C72 C65 C66 107.3(5) . . ? C72 C65 C83 126.2(6) . . ? C66 C65 C83 126.5(5) . . ? C73 C66 C67 119.0(5) . . ? C73 C66 C65 131.3(5) . . ? C67 C66 C65 109.6(5) . . ? C76 C67 C66 121.7(5) . . ? C76 C67 C68 132.4(6) . . ? C66 C67 C68 105.8(5) . . ? C69 C68 C72 110.6(5) . . ? C69 C68 C67 142.1(6) . . ? C72 C68 C67 107.3(5) . . ? C68 C69 C70 106.1(5) . . ? C68 C69 C90 127.5(5) . . ? C70 C69 C90 126.4(5) . . ? C81 C70 C71 119.8(5) . . ? C81 C70 C69 130.2(5) . . ? C71 C70 C69 109.8(5) . . ? C78 C71 C70 120.6(5) . . ? C78 C71 C72 133.1(5) . . ? C70 C71 C72 106.2(5) . . ? C65 C72 C68 109.8(5) . . ? C65 C72 C71 142.7(6) . . ? C68 C72 C71 107.2(5) . . ? C66 C73 C74 120.2(5) . . ? C66 C73 H53 119.9 . . ? C74 C73 H53 119.9 . . ? C75 C74 C73 119.9(5) . . ? C75 C74 H54 120.1 . . ? C73 C74 H54 120.1 . . ? C74 C75 O9 125.3(5) . . ? C74 C75 C76 121.5(5) . . ? O9 C75 C76 113.1(5) . . ? C67 C76 C75 117.6(5) . . ? C67 C76 H55 121.2 . . ? C75 C76 H55 121.2 . . ? C75 O9 C77 116.4(5) . . ? O9 C77 H56 109.5 . . ? O9 C77 H57 109.5 . . ? H56 C77 H57 109.5 . . ? O9 C77 H58 109.5 . . ? H56 C77 H58 109.5 . . ? H57 C77 H58 109.5 . . ? C71 C78 C79 118.6(5) . . ? C71 C78 H59 120.7 . . ? C79 C78 H59 120.7 . . ? O10 C79 C80 124.7(5) . . ? O10 C79 C78 114.2(5) . . ? C80 C79 C78 121.0(5) . . ? C79 C80 C81 120.6(5) . . ? C79 C80 H60 119.7 . . ? C81 C80 H60 119.7 . . ? C70 C81 C80 119.3(6) . . ? C70 C81 H61 120.4 . . ? C80 C81 H61 120.4 . . ? C79 O10 C82 116.5(5) . . ? C88 C83 C84 119.6(6) . . ? C88 C83 C65 120.9(5) . . ? C84 C83 C65 119.4(5) . . ? C85 C84 C83 118.9(6) . . ? C85 C84 H62 120.5 . . ? C83 C84 H62 120.5 . . ? O11 C85 C84 124.4(6) . . ? O11 C85 C86 114.9(6) . . ? C84 C85 C86 120.7(6) . . ? C87 C86 C85 119.8(6) . . ? C87 C86 H63 120.1 . . ? C85 C86 H63 120.1 . . ? C86 C87 C88 120.3(6) . . ? C86 C87 H64 119.8 . . ? C88 C87 H64 119.8 . . ? C83 C88 C87 120.6(6) . . ? C83 C88 H65 119.7 . . ? C87 C88 H65 119.7 . . ? C85 O11 C89 116.3(6) . . ? O11 C89 H66 109.5 . . ? O11 C89 H67 109.5 . . ? H66 C89 H67 109.5 . . ? O11 C89 H68 109.5 . . ? H66 C89 H68 109.5 . . ? H67 C89 H68 109.5 . . ? C91 C90 C95 120.2(6) . . ? C91 C90 C69 119.8(5) . . ? C95 C90 C69 120.0(5) . . ? C90 C91 C92 120.9(6) . . ? C90 C91 H69 119.5 . . ? C92 C91 H69 119.5 . . ? O12 C92 C93 124.8(6) . . ? O12 C92 C91 115.9(5) . . ? C93 C92 C91 119.3(6) . . ? C92 C93 C94 119.1(6) . . ? C92 C93 H70 120.4 . . ? C94 C93 H70 120.4 . . ? C95 C94 C93 121.1(6) . . ? C95 C94 H71 119.5 . . ? C93 C94 H71 119.5 . . ? C94 C95 C90 119.3(6) . . ? C94 C95 H72 120.3 . . ? C90 C95 H72 120.3 . . ? C92 O12 C96 117.4(5) . . ? O12 C96 H73 109.5 . . ? O12 C96 H74 109.5 . . ? H73 C96 H74 109.5 . . ? O12 C96 H75 109.5 . . ? H73 C96 H75 109.5 . . ? H74 C96 H75 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 C9 -176.7(6) . . . . ? C19 C1 C2 C9 5.3(10) . . . . ? C8 C1 C2 C3 1.9(6) . . . . ? C19 C1 C2 C3 -176.1(5) . . . . ? C9 C2 C3 C12 0.4(8) . . . . ? C1 C2 C3 C12 -178.4(5) . . . . ? C9 C2 C3 C4 177.7(5) . . . . ? C1 C2 C3 C4 -1.1(6) . . . . ? C12 C3 C4 C5 -1.0(12) . . . . ? C2 C3 C4 C5 -177.9(7) . . . . ? C12 C3 C4 C8 176.9(6) . . . . ? C2 C3 C4 C8 -0.1(6) . . . . ? C3 C4 C5 C6 178.3(7) . . . . ? C8 C4 C5 C6 0.5(6) . . . . ? C3 C4 C5 C26 -1.3(12) . . . . ? C8 C4 C5 C26 -179.1(5) . . . . ? C4 C5 C6 C14 178.9(6) . . . . ? C26 C5 C6 C14 -1.5(10) . . . . ? C4 C5 C6 C7 0.6(6) . . . . ? C26 C5 C6 C7 -179.8(5) . . . . ? C14 C6 C7 C17 0.1(9) . . . . ? C5 C6 C7 C17 178.7(5) . . . . ? C14 C6 C7 C8 -180.0(5) . . . . ? C5 C6 C7 C8 -1.4(6) . . . . ? C19 C1 C8 C7 -1.8(12) . . . . ? C2 C1 C8 C7 -179.8(7) . . . . ? C19 C1 C8 C4 176.1(5) . . . . ? C2 C1 C8 C4 -1.9(6) . . . . ? C17 C7 C8 C1 -0.4(12) . . . . ? C6 C7 C8 C1 179.7(7) . . . . ? C17 C7 C8 C4 -178.4(6) . . . . ? C6 C7 C8 C4 1.7(6) . . . . ? C5 C4 C8 C1 179.9(5) . . . . ? C3 C4 C8 C1 1.3(6) . . . . ? C5 C4 C8 C7 -1.4(6) . . . . ? C3 C4 C8 C7 180.0(4) . . . . ? C3 C2 C9 C10 0.1(8) . . . . ? C1 C2 C9 C10 178.5(6) . . . . ? C2 C9 C10 C11 0.1(8) . . . . ? C9 C10 C11 O1 179.7(5) . . . . ? C9 C10 C11 C12 -0.8(8) . . . . ? C2 C3 C12 C11 -1.0(8) . . . . ? C4 C3 C12 C11 -177.5(5) . . . . ? O1 C11 C12 C3 -179.3(5) . . . . ? C10 C11 C12 C3 1.2(8) . . . . ? C10 C11 O1 C13 -4.9(8) . . . . ? C12 C11 O1 C13 175.5(5) . . . . ? C7 C6 C14 C15 0.2(8) . . . . ? C5 C6 C14 C15 -178.0(5) . . . . ? C6 C14 C15 C16 -0.5(8) . . . . ? C14 C15 C16 O2 179.7(5) . . . . ? C14 C15 C16 C17 0.4(8) . . . . ? C6 C7 C17 C16 -0.2(8) . . . . ? C8 C7 C17 C16 179.9(6) . . . . ? O2 C16 C17 C7 -179.4(5) . . . . ? C15 C16 C17 C7 -0.1(8) . . . . ? C15 C16 O2 C18 2.1(8) . . . . ? C17 C16 O2 C18 -178.6(5) . . . . ? C8 C1 C19 C20 -131.8(6) . . . . ? C2 C1 C19 C20 45.8(8) . . . . ? C8 C1 C19 C24 45.7(8) . . . . ? C2 C1 C19 C24 -136.7(6) . . . . ? C24 C19 C20 C21 -2.3(8) . . . . ? C1 C19 C20 C21 175.2(5) . . . . ? C19 C20 C21 O3 -178.4(5) . . . . ? C19 C20 C21 C22 0.9(9) . . . . ? O3 C21 C22 C23 -179.9(5) . . . . ? C20 C21 C22 C23 0.8(9) . . . . ? C21 C22 C23 C24 -1.1(9) . . . . ? C22 C23 C24 C19 -0.3(9) . . . . ? C20 C19 C24 C23 2.1(8) . . . . ? C1 C19 C24 C23 -175.4(5) . . . . ? C22 C21 O3 C25 -1.0(9) . . . . ? C20 C21 O3 C25 178.3(5) . . . . ? C4 C5 C26 C31 -49.4(9) . . . . ? C6 C5 C26 C31 131.0(6) . . . . ? C4 C5 C26 C27 132.0(6) . . . . ? C6 C5 C26 C27 -47.5(8) . . . . ? C31 C26 C27 C28 1.0(9) . . . . ? C5 C26 C27 C28 179.6(5) . . . . ? C26 C27 C28 O4 -179.0(6) . . . . ? C26 C27 C28 C29 -1.8(9) . . . . ? O4 C28 C29 C30 180.0(6) . . . . ? C27 C28 C29 C30 2.5(9) . . . . ? C28 C29 C30 C31 -2.5(10) . . . . ? C29 C30 C31 C26 1.7(9) . . . . ? C27 C26 C31 C30 -1.0(9) . . . . ? C5 C26 C31 C30 -179.5(5) . . . . ? C27 C28 O4 C32 -6.6(9) . . . . ? C29 C28 O4 C32 176.1(6) . . . . ? C36 C33 C34 C37 -176.6(6) 2_657 . . . ? C42 C33 C34 C37 9.1(10) . . . . ? C36 C33 C34 C35 2.0(6) 2_657 . . . ? C42 C33 C34 C35 -172.3(5) . . . . ? C37 C34 C35 C40 -1.6(8) . . . . ? C33 C34 C35 C40 179.6(5) . . . . ? C37 C34 C35 C36 177.4(5) . . . . ? C33 C34 C35 C36 -1.4(6) . . . . ? C40 C35 C36 C33 0.6(13) . . . 2_657 ? C34 C35 C36 C33 -178.2(8) . . . 2_657 ? C40 C35 C36 C36 179.1(7) . . . 2_657 ? C34 C35 C36 C36 0.3(7) . . . 2_657 ? C35 C34 C37 C38 1.3(8) . . . . ? C33 C34 C37 C38 179.8(6) . . . . ? C34 C37 C38 C39 0.6(8) . . . . ? C37 C38 C39 O5 178.5(5) . . . . ? C37 C38 C39 C40 -2.2(8) . . . . ? C34 C35 C40 C39 0.0(8) . . . . ? C36 C35 C40 C39 -178.7(6) . . . . ? O5 C39 C40 C35 -178.7(5) . . . . ? C38 C39 C40 C35 1.9(8) . . . . ? C38 C39 O5 C41 3.4(8) . . . . ? C40 C39 O5 C41 -176.0(5) . . . . ? C36 C33 C42 C43 -127.1(7) 2_657 . . . ? C34 C33 C42 C43 46.1(8) . . . . ? C36 C33 C42 C47 49.1(9) 2_657 . . . ? C34 C33 C42 C47 -137.7(6) . . . . ? C47 C42 C43 C44 -0.8(9) . . . . ? C33 C42 C43 C44 175.5(5) . . . . ? C42 C43 C44 O6 -178.9(5) . . . . ? C42 C43 C44 C45 -0.9(9) . . . . ? O6 C44 C45 C46 -179.1(6) . . . . ? C43 C44 C45 C46 3.1(9) . . . . ? C44 C45 C46 C47 -3.6(9) . . . . ? C45 C46 C47 C42 2.0(9) . . . . ? C43 C42 C47 C46 0.3(9) . . . . ? C33 C42 C47 C46 -175.9(5) . . . . ? C43 C44 O6 C48 179.7(5) . . . . ? C45 C44 O6 C48 1.7(9) . . . . ? C51 C49 C50 C50 -1.9(8) . . . 2_667 ? C58 C49 C50 C50 178.6(6) . . . 2_667 ? C51 C49 C50 C56 -176.1(7) . . . . ? C58 C49 C50 C56 4.4(12) . . . . ? C50 C49 C51 C52 -177.1(6) . . . . ? C58 C49 C51 C52 2.4(10) . . . . ? C50 C49 C51 C56 -0.6(6) . . . 2_667 ? C58 C49 C51 C56 178.9(5) . . . 2_667 ? C56 C51 C52 C53 1.2(8) 2_667 . . 2_667 ? C49 C51 C52 C53 177.4(6) . . . 2_667 ? C52 C53 C54 O7 178.5(5) 2_667 . . . ? C52 C53 C54 C55 0.3(9) 2_667 . . . ? O7 C54 C55 C56 -179.4(5) . . . . ? C53 C54 C55 C56 -1.0(9) . . . . ? C54 C55 C56 C51 0.6(9) . . . 2_667 ? C54 C55 C56 C50 -179.1(6) . . . . ? C49 C50 C56 C55 -2.1(13) . . . . ? C50 C50 C56 C55 -176.4(7) 2_667 . . . ? C49 C50 C56 C51 178.2(7) . . . 2_667 ? C50 C50 C56 C51 3.8(7) 2_667 . . 2_667 ? C53 C54 O7 C57 2.9(9) . . . . ? C55 C54 O7 C57 -178.8(5) . . . . ? C50 C49 C58 C63 43.7(9) . . . . ? C51 C49 C58 C63 -135.7(6) . . . . ? C50 C49 C58 C59 -135.8(6) . . . . ? C51 C49 C58 C59 44.8(9) . . . . ? C63 C58 C59 C60 -1.7(9) . . . . ? C49 C58 C59 C60 177.9(5) . . . . ? C58 C59 C60 O8 179.6(5) . . . . ? C58 C59 C60 C61 0.3(9) . . . . ? O8 C60 C61 C62 -178.4(6) . . . . ? C59 C60 C61 C62 0.8(9) . . . . ? C60 C61 C62 C63 -0.5(9) . . . . ? C59 C58 C63 C62 2.0(9) . . . . ? C49 C58 C63 C62 -177.5(6) . . . . ? C61 C62 C63 C58 -0.9(10) . . . . ? C61 C60 O8 C64 -2.6(9) . . . . ? C59 C60 O8 C64 178.1(5) . . . . ? C72 C65 C66 C73 176.9(6) . . . . ? C83 C65 C66 C73 -4.5(10) . . . . ? C72 C65 C66 C67 -0.8(6) . . . . ? C83 C65 C66 C67 177.7(5) . . . . ? C73 C66 C67 C76 2.3(8) . . . . ? C65 C66 C67 C76 -179.6(5) . . . . ? C73 C66 C67 C68 -178.9(5) . . . . ? C65 C66 C67 C68 -0.8(6) . . . . ? C76 C67 C68 C69 0.9(12) . . . . ? C66 C67 C68 C69 -177.7(7) . . . . ? C76 C67 C68 C72 -179.3(6) . . . . ? C66 C67 C68 C72 2.1(6) . . . . ? C72 C68 C69 C70 -1.7(6) . . . . ? C67 C68 C69 C70 178.2(7) . . . . ? C72 C68 C69 C90 176.7(5) . . . . ? C67 C68 C69 C90 -3.4(12) . . . . ? C68 C69 C70 C81 -175.4(6) . . . . ? C90 C69 C70 C81 6.2(10) . . . . ? C68 C69 C70 C71 0.7(6) . . . . ? C90 C69 C70 C71 -177.7(5) . . . . ? C81 C70 C71 C78 -1.8(8) . . . . ? C69 C70 C71 C78 -178.4(5) . . . . ? C81 C70 C71 C72 177.1(5) . . . . ? C69 C70 C71 C72 0.5(6) . . . . ? C66 C65 C72 C68 2.2(6) . . . . ? C83 C65 C72 C68 -176.4(5) . . . . ? C66 C65 C72 C71 174.5(7) . . . . ? C83 C65 C72 C71 -4.0(12) . . . . ? C69 C68 C72 C65 177.2(5) . . . . ? C67 C68 C72 C65 -2.7(6) . . . . ? C69 C68 C72 C71 2.0(6) . . . . ? C67 C68 C72 C71 -177.9(4) . . . . ? C78 C71 C72 C65 4.8(12) . . . . ? C70 C71 C72 C65 -174.0(7) . . . . ? C78 C71 C72 C68 177.3(6) . . . . ? C70 C71 C72 C68 -1.5(6) . . . . ? C67 C66 C73 C74 -0.5(8) . . . . ? C65 C66 C73 C74 -178.1(5) . . . . ? C66 C73 C74 C75 -1.7(8) . . . . ? C73 C74 C75 O9 -179.6(5) . . . . ? C73 C74 C75 C76 2.2(8) . . . . ? C66 C67 C76 C75 -1.8(8) . . . . ? C68 C67 C76 C75 179.8(6) . . . . ? C74 C75 C76 C67 -0.5(8) . . . . ? O9 C75 C76 C67 -178.8(5) . . . . ? C74 C75 O9 C77 0.0(8) . . . . ? C76 C75 O9 C77 178.3(5) . . . . ? C70 C71 C78 C79 1.5(8) . . . . ? C72 C71 C78 C79 -177.0(5) . . . . ? C71 C78 C79 O10 179.6(5) . . . . ? C71 C78 C79 C80 -1.9(8) . . . . ? O10 C79 C80 C81 -179.1(5) . . . . ? C78 C79 C80 C81 2.5(8) . . . . ? C71 C70 C81 C80 2.3(8) . . . . ? C69 C70 C81 C80 178.2(5) . . . . ? C79 C80 C81 C70 -2.7(8) . . . . ? C80 C79 O10 C82 1.6(8) . . . . ? C78 C79 O10 C82 -179.9(5) . . . . ? C72 C65 C83 C88 -43.6(9) . . . . ? C66 C65 C83 C88 138.1(6) . . . . ? C72 C65 C83 C84 132.9(6) . . . . ? C66 C65 C83 C84 -45.5(8) . . . . ? C88 C83 C84 C85 0.9(9) . . . . ? C65 C83 C84 C85 -175.6(5) . . . . ? C83 C84 C85 O11 -178.8(5) . . . . ? C83 C84 C85 C86 2.0(9) . . . . ? O11 C85 C86 C87 177.3(6) . . . . ? C84 C85 C86 C87 -3.4(9) . . . . ? C85 C86 C87 C88 1.9(10) . . . . ? C84 C83 C88 C87 -2.5(9) . . . . ? C65 C83 C88 C87 174.0(6) . . . . ? C86 C87 C88 C83 1.1(10) . . . . ? C84 C85 O11 C89 2.6(9) . . . . ? C86 C85 O11 C89 -178.2(6) . . . . ? C68 C69 C90 C91 -133.4(6) . . . . ? C70 C69 C90 C91 44.7(8) . . . . ? C68 C69 C90 C95 48.2(8) . . . . ? C70 C69 C90 C95 -133.7(6) . . . . ? C95 C90 C91 C92 -2.9(9) . . . . ? C69 C90 C91 C92 178.7(5) . . . . ? C90 C91 C92 O12 -178.6(5) . . . . ? C90 C91 C92 C93 2.2(9) . . . . ? O12 C92 C93 C94 -179.5(6) . . . . ? C91 C92 C93 C94 -0.3(9) . . . . ? C92 C93 C94 C95 -0.7(9) . . . . ? C93 C94 C95 C90 -0.1(9) . . . . ? C91 C90 C95 C94 1.9(8) . . . . ? C69 C90 C95 C94 -179.8(5) . . . . ? C93 C92 O12 C96 -1.5(9) . . . . ? C91 C92 O12 C96 179.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.555 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.089 data_2f _database_code_depnum_ccdc_archive 'CCDC 917510' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H34 O8' _chemical_formula_weight 594.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.380(3) _cell_length_b 8.787(2) _cell_length_c 15.360(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.613(3) _cell_angle_gamma 90.00 _cell_volume 1428.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 2820 _cell_measurement_theta_min 3.0134 _cell_measurement_theta_max 25.3458 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9903 _exptl_absorpt_correction_T_max 0.9951 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9082 _diffrn_reflns_av_R_equivalents 0.1014 _diffrn_reflns_av_sigmaI/netI 0.1159 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2502 _reflns_number_gt 1557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1291P)^2^+29.8866P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2502 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1671 _refine_ls_R_factor_gt 0.1478 _refine_ls_wR_factor_ref 0.4444 _refine_ls_wR_factor_gt 0.4388 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0974(8) -0.0558(10) 0.4391(6) 0.0168(19) Uani 1 1 d . . . C2 C 0.0506(8) 0.0375(10) 0.4907(6) 0.0149(19) Uani 1 1 d . . . C3 C 0.0725(8) 0.1858(10) 0.5360(6) 0.0166(19) Uani 1 1 d . . . C4 C 0.1538(8) 0.3022(10) 0.5411(6) 0.018(2) Uani 1 1 d . . . H1 H 0.2133 0.2942 0.5113 0.022 Uiso 1 1 calc R . . C5 C 0.1486(8) 0.4344(10) 0.5911(6) 0.018(2) Uani 1 1 d . . . C6 C 0.0660(8) 0.4468(10) 0.6385(6) 0.019(2) Uani 1 1 d . . . H2 H 0.0646 0.5361 0.6730 0.023 Uiso 1 1 calc R . . C7 C -0.0161(8) 0.3230(10) 0.6343(5) 0.0121(18) Uani 1 1 d . . . C8 C -0.0181(8) 0.1949(9) 0.5813(5) 0.0109(17) Uani 1 1 d . . . O1 O -0.0900(6) 0.3224(7) 0.6871(4) 0.0222(16) Uani 1 1 d . . . C9 C -0.1339(9) 0.4653(11) 0.7072(7) 0.023(2) Uani 1 1 d . . . H3 H -0.0630 0.5217 0.7519 0.034 Uiso 1 1 calc R . . H4 H -0.1985 0.4482 0.7341 0.034 Uiso 1 1 calc R . . H5 H -0.1702 0.5242 0.6492 0.034 Uiso 1 1 calc R . . O2 O 0.2338(6) 0.5459(7) 0.5931(4) 0.0222(16) Uani 1 1 d . . . C10 C 0.2289(10) 0.6847(11) 0.6405(7) 0.026(2) Uani 1 1 d . . . H6 H 0.1430 0.7263 0.6149 0.039 Uiso 1 1 calc R . . H7 H 0.2881 0.7584 0.6315 0.039 Uiso 1 1 calc R . . H8 H 0.2522 0.6645 0.7075 0.039 Uiso 1 1 calc R . . C11 C 0.2039(8) -0.0247(10) 0.4105(6) 0.0156(19) Uani 1 1 d . . . C12 C 0.2086(8) 0.1130(10) 0.3667(6) 0.0165(19) Uani 1 1 d . . . H9 H 0.1423 0.1850 0.3552 0.020 Uiso 1 1 calc R . . C13 C 0.3116(8) 0.1458(11) 0.3394(6) 0.019(2) Uani 1 1 d . . . C14 C 0.4079(8) 0.0406(11) 0.3580(6) 0.019(2) Uani 1 1 d . . . H10 H 0.4789 0.0626 0.3416 0.023 Uiso 1 1 calc R . . C15 C 0.4016(8) -0.0976(10) 0.4006(6) 0.018(2) Uani 1 1 d . . . C16 C 0.3027(9) -0.1300(11) 0.4273(6) 0.020(2) Uani 1 1 d . . . H11 H 0.3006 -0.2239 0.4573 0.024 Uiso 1 1 calc R . . O3 O 0.3060(6) 0.2811(8) 0.2962(5) 0.0231(16) Uani 1 1 d . . . C17 C 0.3955(10) 0.3080(13) 0.2541(8) 0.032(3) Uani 1 1 d . . . H12 H 0.4789 0.3246 0.3029 0.048 Uiso 1 1 calc R . . H13 H 0.3707 0.3983 0.2140 0.048 Uiso 1 1 calc R . . H14 H 0.3989 0.2196 0.2161 0.048 Uiso 1 1 calc R . . O4 O 0.5026(6) -0.1912(7) 0.4117(5) 0.0221(16) Uani 1 1 d . . . C18 C 0.4989(9) -0.3367(10) 0.4502(7) 0.020(2) Uani 1 1 d . . . H15 H 0.4999 -0.3252 0.5140 0.030 Uiso 1 1 calc R . . H16 H 0.5727 -0.3960 0.4519 0.030 Uiso 1 1 calc R . . H17 H 0.4215 -0.3897 0.4114 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(5) 0.016(5) 0.014(4) 0.000(4) 0.009(4) 0.001(4) C2 0.017(4) 0.015(5) 0.014(4) 0.001(3) 0.007(3) 0.001(4) C3 0.022(5) 0.014(5) 0.018(4) -0.001(4) 0.011(4) 0.003(4) C4 0.018(4) 0.021(5) 0.020(5) -0.001(4) 0.012(4) -0.001(4) C5 0.021(5) 0.019(5) 0.014(4) 0.000(4) 0.008(4) -0.003(4) C6 0.022(5) 0.017(5) 0.020(5) 0.000(4) 0.009(4) 0.000(4) C7 0.013(4) 0.017(4) 0.009(4) 0.002(3) 0.006(3) 0.001(3) C8 0.012(4) 0.013(4) 0.009(4) 0.000(3) 0.006(3) 0.001(3) O1 0.033(4) 0.020(3) 0.025(3) -0.004(3) 0.023(3) -0.001(3) C9 0.027(5) 0.023(5) 0.023(5) -0.002(4) 0.015(4) 0.003(4) O2 0.028(4) 0.016(3) 0.026(4) -0.007(3) 0.013(3) -0.007(3) C10 0.039(6) 0.014(5) 0.021(5) -0.003(4) 0.006(4) -0.002(4) C11 0.019(4) 0.020(5) 0.010(4) -0.005(4) 0.009(3) -0.005(4) C12 0.017(4) 0.020(5) 0.016(4) -0.004(4) 0.011(4) 0.001(4) C13 0.020(5) 0.027(5) 0.015(4) 0.000(4) 0.011(4) -0.007(4) C14 0.018(5) 0.024(5) 0.017(4) 0.000(4) 0.008(4) 0.000(4) C15 0.020(4) 0.018(5) 0.019(4) -0.001(4) 0.009(4) 0.004(4) C16 0.026(5) 0.018(5) 0.017(4) 0.000(4) 0.009(4) -0.002(4) O3 0.023(4) 0.024(4) 0.031(4) 0.005(3) 0.020(3) 0.002(3) C17 0.035(6) 0.035(6) 0.037(6) 0.013(5) 0.027(5) 0.000(5) O4 0.020(3) 0.018(3) 0.030(4) 0.004(3) 0.012(3) 0.008(3) C18 0.017(5) 0.015(5) 0.029(5) 0.002(4) 0.010(4) 0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.377(12) . ? C1 C11 1.459(12) . ? C1 C8 1.483(12) 3_556 ? C2 C2 1.444(17) 3_556 ? C2 C3 1.455(12) . ? C3 C4 1.362(13) . ? C3 C8 1.443(11) . ? C4 C5 1.405(13) . ? C4 H1 0.9500 . ? C5 O2 1.370(11) . ? C5 C6 1.390(12) . ? C6 C7 1.420(12) . ? C6 H2 0.9500 . ? C7 O1 1.367(10) . ? C7 C8 1.385(12) . ? C8 C1 1.483(12) 3_556 ? O1 C9 1.426(11) . ? C9 H3 0.9800 . ? C9 H4 0.9800 . ? C9 H5 0.9800 . ? O2 C10 1.432(11) . ? C10 H6 0.9800 . ? C10 H7 0.9800 . ? C10 H8 0.9800 . ? C11 C12 1.395(13) . ? C11 C16 1.405(13) . ? C12 C13 1.412(12) . ? C12 H9 0.9500 . ? C13 O3 1.352(11) . ? C13 C14 1.381(13) . ? C14 C15 1.394(13) . ? C14 H10 0.9500 . ? C15 C16 1.362(13) . ? C15 O4 1.373(11) . ? C16 H11 0.9500 . ? O3 C17 1.413(11) . ? C17 H12 0.9800 . ? C17 H13 0.9800 . ? C17 H14 0.9800 . ? O4 C18 1.416(11) . ? C18 H15 0.9800 . ? C18 H16 0.9800 . ? C18 H17 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11 127.0(8) . . ? C2 C1 C8 106.1(7) . 3_556 ? C11 C1 C8 126.8(8) . 3_556 ? C1 C2 C2 110.4(10) . 3_556 ? C1 C2 C3 140.7(8) . . ? C2 C2 C3 108.8(9) 3_556 . ? C4 C3 C8 121.4(8) . . ? C4 C3 C2 133.9(8) . . ? C8 C3 C2 104.7(7) . . ? C3 C4 C5 119.2(8) . . ? C3 C4 H1 120.4 . . ? C5 C4 H1 120.4 . . ? O2 C5 C6 122.8(8) . . ? O2 C5 C4 115.6(8) . . ? C6 C5 C4 121.6(8) . . ? C5 C6 C7 118.5(8) . . ? C5 C6 H2 120.8 . . ? C7 C6 H2 120.8 . . ? O1 C7 C8 117.7(7) . . ? O1 C7 C6 121.0(8) . . ? C8 C7 C6 121.2(7) . . ? C7 C8 C3 117.9(7) . . ? C7 C8 C1 132.2(7) . 3_556 ? C3 C8 C1 109.9(7) . 3_556 ? C7 O1 C9 117.7(7) . . ? O1 C9 H3 109.5 . . ? O1 C9 H4 109.5 . . ? H3 C9 H4 109.5 . . ? O1 C9 H5 109.5 . . ? H3 C9 H5 109.5 . . ? H4 C9 H5 109.5 . . ? C5 O2 C10 117.4(7) . . ? O2 C10 H6 109.5 . . ? O2 C10 H7 109.5 . . ? H6 C10 H7 109.5 . . ? O2 C10 H8 109.5 . . ? H6 C10 H8 109.5 . . ? H7 C10 H8 109.5 . . ? C12 C11 C16 119.3(8) . . ? C12 C11 C1 119.4(8) . . ? C16 C11 C1 121.3(8) . . ? C11 C12 C13 120.2(8) . . ? C11 C12 H9 119.9 . . ? C13 C12 H9 119.9 . . ? O3 C13 C14 125.4(8) . . ? O3 C13 C12 115.6(8) . . ? C14 C13 C12 119.0(9) . . ? C13 C14 C15 120.3(8) . . ? C13 C14 H10 119.8 . . ? C15 C14 H10 119.8 . . ? C16 C15 O4 125.8(8) . . ? C16 C15 C14 121.0(8) . . ? O4 C15 C14 113.2(8) . . ? C15 C16 C11 120.1(9) . . ? C15 C16 H11 120.0 . . ? C11 C16 H11 120.0 . . ? C13 O3 C17 117.4(7) . . ? O3 C17 H12 109.5 . . ? O3 C17 H13 109.5 . . ? H12 C17 H13 109.5 . . ? O3 C17 H14 109.5 . . ? H12 C17 H14 109.5 . . ? H13 C17 H14 109.5 . . ? C15 O4 C18 116.1(7) . . ? O4 C18 H15 109.5 . . ? O4 C18 H16 109.5 . . ? H15 C18 H16 109.5 . . ? O4 C18 H17 109.5 . . ? H15 C18 H17 109.5 . . ? H16 C18 H17 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C2 -176.5(9) . . . 3_556 ? C8 C1 C2 C2 3.2(12) 3_556 . . 3_556 ? C11 C1 C2 C3 0.4(18) . . . . ? C8 C1 C2 C3 -179.9(10) 3_556 . . . ? C1 C2 C3 C4 3.6(19) . . . . ? C2 C2 C3 C4 -179.4(10) 3_556 . . . ? C1 C2 C3 C8 -176.9(11) . . . . ? C2 C2 C3 C8 0.0(11) 3_556 . . . ? C8 C3 C4 C5 -0.4(13) . . . . ? C2 C3 C4 C5 179.0(9) . . . . ? C3 C4 C5 O2 179.8(8) . . . . ? C3 C4 C5 C6 2.6(13) . . . . ? O2 C5 C6 C7 -178.2(8) . . . . ? C4 C5 C6 C7 -1.2(13) . . . . ? C5 C6 C7 O1 173.3(8) . . . . ? C5 C6 C7 C8 -2.5(12) . . . . ? O1 C7 C8 C3 -171.4(7) . . . . ? C6 C7 C8 C3 4.5(12) . . . . ? O1 C7 C8 C1 7.8(13) . . . 3_556 ? C6 C7 C8 C1 -176.3(9) . . . 3_556 ? C4 C3 C8 C7 -3.1(12) . . . . ? C2 C3 C8 C7 177.3(7) . . . . ? C4 C3 C8 C1 177.6(8) . . . 3_556 ? C2 C3 C8 C1 -2.0(9) . . . 3_556 ? C8 C7 O1 C9 -152.6(8) . . . . ? C6 C7 O1 C9 31.5(11) . . . . ? C6 C5 O2 C10 -5.0(12) . . . . ? C4 C5 O2 C10 177.9(8) . . . . ? C2 C1 C11 C12 -50.4(13) . . . . ? C8 C1 C11 C12 129.9(9) 3_556 . . . ? C2 C1 C11 C16 128.7(10) . . . . ? C8 C1 C11 C16 -50.9(12) 3_556 . . . ? C16 C11 C12 C13 0.1(12) . . . . ? C1 C11 C12 C13 179.3(8) . . . . ? C11 C12 C13 O3 179.0(7) . . . . ? C11 C12 C13 C14 -0.9(13) . . . . ? O3 C13 C14 C15 -178.0(8) . . . . ? C12 C13 C14 C15 1.8(13) . . . . ? C13 C14 C15 C16 -2.0(13) . . . . ? C13 C14 C15 O4 178.2(8) . . . . ? O4 C15 C16 C11 -179.0(8) . . . . ? C14 C15 C16 C11 1.2(13) . . . . ? C12 C11 C16 C15 -0.3(13) . . . . ? C1 C11 C16 C15 -179.4(8) . . . . ? C14 C13 O3 C17 10.0(13) . . . . ? C12 C13 O3 C17 -169.8(8) . . . . ? C16 C15 O4 C18 3.3(13) . . . . ? C14 C15 O4 C18 -176.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.872 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.147 data_2bd _database_code_depnum_ccdc_archive 'CCDC 917511' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H20 F6 O2' _chemical_formula_weight 550.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.550(5) _cell_length_b 7.3020(18) _cell_length_c 18.848(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.759(5) _cell_angle_gamma 90.00 _cell_volume 2407.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3591 _cell_measurement_theta_min 3.0229 _cell_measurement_theta_max 25.3132 _exptl_crystal_description Platelet _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9814 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15510 _diffrn_reflns_av_R_equivalents 0.1178 _diffrn_reflns_av_sigmaI/netI 0.1035 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4231 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0847P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4231 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1803 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1246(2) 0.1951(4) 0.74380(19) 0.0169(8) Uani 1 1 d . . . C2 C 0.19323(19) 0.1890(4) 0.79519(18) 0.0159(8) Uani 1 1 d . . . C3 C 0.1978(2) 0.1878(4) 0.86863(19) 0.0170(8) Uani 1 1 d . . . H1 H 0.1529 0.1839 0.8935 0.020 Uiso 1 1 calc R . . C4 C 0.2705(2) 0.1925(4) 0.90566(18) 0.0174(8) Uani 1 1 d . . . C5 C 0.3359(2) 0.1998(4) 0.87023(19) 0.0195(8) Uani 1 1 d . . . H2 H 0.3845 0.2026 0.8965 0.023 Uiso 1 1 calc R . . C6 C 0.3312(2) 0.2031(4) 0.79532(19) 0.0191(8) Uani 1 1 d . . . H3 H 0.3763 0.2098 0.7708 0.023 Uiso 1 1 calc R . . C7 C 0.25993(19) 0.1964(4) 0.75764(19) 0.0173(8) Uani 1 1 d . . . C8 C 0.23322(19) 0.2041(4) 0.68189(19) 0.0168(8) Uani 1 1 d . . . C9 C 0.25843(19) 0.2098(4) 0.61450(19) 0.0171(8) Uani 1 1 d . . . C10 C 0.18858(19) 0.2122(4) 0.56377(19) 0.0175(8) Uani 1 1 d . . . C11 C 0.1807(2) 0.2061(4) 0.49015(19) 0.0190(8) Uani 1 1 d . . . H4 H 0.2243 0.2031 0.4635 0.023 Uiso 1 1 calc R . . C12 C 0.1065(2) 0.2045(4) 0.45597(19) 0.0191(8) Uani 1 1 d . . . C13 C 0.0427(2) 0.2064(4) 0.4935(2) 0.0220(8) Uani 1 1 d . . . H5 H -0.0068 0.2066 0.4687 0.026 Uiso 1 1 calc R . . C14 C 0.05008(19) 0.2082(4) 0.5677(2) 0.0211(8) Uani 1 1 d . . . H6 H 0.0061 0.2073 0.5939 0.025 Uiso 1 1 calc R . . C15 C 0.12206(19) 0.2112(4) 0.60256(18) 0.0168(8) Uani 1 1 d . . . C16 C 0.1503(2) 0.2058(4) 0.67785(19) 0.0170(8) Uani 1 1 d . . . O1 O 0.26917(13) 0.1870(3) 0.97869(13) 0.0238(6) Uani 1 1 d . . . C17 C 0.3407(2) 0.1995(5) 1.0204(2) 0.0254(9) Uani 1 1 d . . . H7 H 0.3742 0.0998 1.0074 0.038 Uiso 1 1 calc R . . H8 H 0.3322 0.1898 1.0710 0.038 Uiso 1 1 calc R . . H9 H 0.3648 0.3174 1.0115 0.038 Uiso 1 1 calc R . . C18 C 0.0984(2) 0.1973(5) 0.3763(2) 0.0233(9) Uani 1 1 d . . . F1 F 0.02496(13) 0.1984(4) 0.34920(13) 0.0484(7) Uani 1 1 d . . . F2 F 0.13149(13) 0.3377(3) 0.34617(12) 0.0366(6) Uani 1 1 d . . . F3 F 0.12906(14) 0.0466(3) 0.35083(12) 0.0442(7) Uani 1 1 d . . . C19 C 0.04540(19) 0.1899(4) 0.76236(18) 0.0167(8) Uani 1 1 d . . . C20 C 0.02184(19) 0.0566(4) 0.80945(19) 0.0185(8) Uani 1 1 d . . . H10 H 0.0580 -0.0281 0.8307 0.022 Uiso 1 1 calc R . . C21 C -0.0540(2) 0.0477(5) 0.82526(19) 0.0225(9) Uani 1 1 d . . . H11 H -0.0694 -0.0437 0.8570 0.027 Uiso 1 1 calc R . . C22 C -0.1071(2) 0.1705(4) 0.7952(2) 0.0199(8) Uani 1 1 d . . . C23 C -0.0845(2) 0.3048(4) 0.7492(2) 0.0203(8) Uani 1 1 d . . . H12 H -0.1208 0.3901 0.7288 0.024 Uiso 1 1 calc R . . C24 C -0.0097(2) 0.3146(4) 0.73294(19) 0.0198(8) Uani 1 1 d . . . H13 H 0.0051 0.4070 0.7014 0.024 Uiso 1 1 calc R . . C25 C -0.1879(2) 0.1633(5) 0.8109(2) 0.0244(9) Uani 1 1 d . . . F4 F -0.20444(13) 0.0222(3) 0.85188(17) 0.0567(8) Uani 1 1 d . . . F5 F -0.21032(13) 0.3111(3) 0.84504(15) 0.0458(7) Uani 1 1 d . . . F6 F -0.23687(13) 0.1512(4) 0.75249(14) 0.0533(7) Uani 1 1 d . . . C26 C 0.33664(19) 0.2092(4) 0.59283(18) 0.0169(8) Uani 1 1 d . . . C27 C 0.3936(2) 0.1001(4) 0.62795(19) 0.0191(8) Uani 1 1 d . . . H14 H 0.3807 0.0241 0.6661 0.023 Uiso 1 1 calc R . . C28 C 0.46795(19) 0.0994(4) 0.60895(19) 0.0189(8) Uani 1 1 d . . . H15 H 0.5052 0.0227 0.6333 0.023 Uiso 1 1 calc R . . C29 C 0.48771(19) 0.2114(4) 0.55410(19) 0.0175(8) Uani 1 1 d . . . C30 C 0.4317(2) 0.3213(4) 0.51786(19) 0.0183(8) Uani 1 1 d . . . H16 H 0.4447 0.3973 0.4798 0.022 Uiso 1 1 calc R . . C31 C 0.3580(2) 0.3192(4) 0.53727(19) 0.0170(8) Uani 1 1 d . . . H17 H 0.3207 0.3944 0.5123 0.020 Uiso 1 1 calc R . . O2 O 0.55943(13) 0.2294(3) 0.53170(14) 0.0238(6) Uani 1 1 d . . . C32 C 0.6187(2) 0.1187(5) 0.5670(2) 0.0293(9) Uani 1 1 d . . . H18 H 0.6237 0.1479 0.6179 0.044 Uiso 1 1 calc R . . H19 H 0.6673 0.1438 0.5466 0.044 Uiso 1 1 calc R . . H20 H 0.6057 -0.0110 0.5605 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0221(19) 0.0150(17) 0.0128(19) -0.0004(14) -0.0030(15) -0.0005(15) C2 0.0185(18) 0.0166(17) 0.0119(19) 0.0018(14) -0.0024(15) 0.0024(15) C3 0.0193(18) 0.0169(17) 0.0140(19) 0.0003(14) -0.0025(15) 0.0001(15) C4 0.025(2) 0.0198(18) 0.0061(17) -0.0011(14) -0.0053(15) 0.0007(16) C5 0.0201(19) 0.0233(19) 0.0143(19) -0.0045(15) -0.0040(15) -0.0007(15) C6 0.0181(18) 0.0248(19) 0.0142(19) -0.0002(15) -0.0002(15) 0.0016(15) C7 0.0178(18) 0.0207(18) 0.0128(19) -0.0010(15) -0.0034(15) 0.0019(15) C8 0.0177(18) 0.0199(18) 0.0124(19) 0.0015(15) -0.0013(15) -0.0036(15) C9 0.0200(19) 0.0159(17) 0.0142(19) -0.0004(15) -0.0049(15) 0.0002(15) C10 0.0181(18) 0.0204(18) 0.0134(19) -0.0008(15) -0.0023(15) 0.0006(15) C11 0.0195(19) 0.0247(19) 0.0127(19) 0.0009(15) 0.0009(15) 0.0002(15) C12 0.025(2) 0.0196(18) 0.0119(19) 0.0017(15) -0.0036(16) 0.0006(16) C13 0.0172(19) 0.030(2) 0.018(2) 0.0024(16) -0.0048(16) -0.0029(16) C14 0.0156(18) 0.031(2) 0.016(2) 0.0004(16) 0.0004(15) 0.0005(16) C15 0.0200(19) 0.0209(18) 0.0095(18) 0.0023(14) 0.0009(15) -0.0011(15) C16 0.0205(19) 0.0170(17) 0.0132(19) -0.0015(15) 0.0002(15) 0.0023(15) O1 0.0233(14) 0.0362(14) 0.0111(14) -0.0005(11) -0.0031(11) -0.0016(11) C17 0.024(2) 0.039(2) 0.012(2) -0.0008(17) -0.0077(16) -0.0001(17) C18 0.022(2) 0.030(2) 0.018(2) 0.0012(17) -0.0001(16) -0.0027(17) F1 0.0242(13) 0.103(2) 0.0170(13) -0.0017(13) -0.0061(10) -0.0061(13) F2 0.0454(15) 0.0432(13) 0.0208(14) 0.0113(10) 0.0006(11) -0.0057(11) F3 0.0683(18) 0.0440(14) 0.0195(14) -0.0088(11) -0.0002(13) 0.0100(13) C19 0.0161(18) 0.0222(18) 0.0108(19) -0.0033(15) -0.0045(15) 0.0012(15) C20 0.0193(19) 0.0235(19) 0.012(2) -0.0001(15) -0.0020(15) 0.0028(15) C21 0.029(2) 0.026(2) 0.012(2) 0.0036(15) -0.0019(17) 0.0003(17) C22 0.0186(19) 0.0231(19) 0.018(2) -0.0048(15) -0.0013(15) -0.0030(16) C23 0.0177(19) 0.0227(19) 0.020(2) 0.0023(16) -0.0031(16) 0.0055(15) C24 0.027(2) 0.0201(18) 0.0114(19) 0.0015(15) -0.0035(16) -0.0026(16) C25 0.025(2) 0.031(2) 0.017(2) -0.0006(17) -0.0026(17) -0.0045(17) F4 0.0296(14) 0.0587(16) 0.085(2) 0.0365(16) 0.0209(14) 0.0064(12) F5 0.0307(13) 0.0547(15) 0.0540(18) -0.0206(13) 0.0150(13) -0.0010(11) F6 0.0251(14) 0.105(2) 0.0291(16) -0.0155(15) -0.0027(11) -0.0079(13) C26 0.0189(19) 0.0199(18) 0.0118(19) -0.0048(14) 0.0001(15) -0.0022(15) C27 0.027(2) 0.0212(18) 0.0084(19) 0.0004(14) -0.0021(16) -0.0031(16) C28 0.0191(19) 0.0190(18) 0.018(2) 0.0027(15) 0.0011(16) -0.0003(15) C29 0.0160(18) 0.0205(18) 0.016(2) -0.0060(15) 0.0033(15) -0.0030(15) C30 0.026(2) 0.0183(18) 0.0102(19) -0.0001(14) -0.0005(15) -0.0018(15) C31 0.0201(19) 0.0172(17) 0.0132(19) 0.0002(14) -0.0023(15) 0.0016(15) O2 0.0167(13) 0.0305(14) 0.0241(15) 0.0015(11) 0.0015(11) 0.0037(11) C32 0.022(2) 0.035(2) 0.031(3) -0.0022(18) 0.0004(18) 0.0021(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C16 1.359(5) . ? C1 C19 1.462(5) . ? C1 C2 1.482(5) . ? C2 C3 1.380(5) . ? C2 C7 1.418(5) . ? C3 C4 1.403(5) . ? C3 H1 0.9500 . ? C4 C5 1.377(5) . ? C4 O1 1.379(4) . ? C5 C6 1.408(5) . ? C5 H2 0.9500 . ? C6 C7 1.387(5) . ? C6 H3 0.9500 . ? C7 C8 1.467(5) . ? C8 C9 1.380(5) . ? C8 C16 1.451(5) . ? C9 C26 1.464(5) . ? C9 C10 1.491(5) . ? C10 C11 1.384(5) . ? C10 C15 1.428(5) . ? C11 C12 1.405(5) . ? C11 H4 0.9500 . ? C12 C13 1.373(5) . ? C12 C18 1.497(5) . ? C13 C14 1.396(5) . ? C13 H5 0.9500 . ? C14 C15 1.374(5) . ? C14 H6 0.9500 . ? C15 C16 1.464(5) . ? O1 C17 1.428(4) . ? C17 H7 0.9800 . ? C17 H8 0.9800 . ? C17 H9 0.9800 . ? C18 F2 1.329(4) . ? C18 F3 1.332(4) . ? C18 F1 1.347(4) . ? C19 C20 1.403(5) . ? C19 C24 1.408(5) . ? C20 C21 1.390(5) . ? C20 H10 0.9500 . ? C21 C22 1.380(5) . ? C21 H11 0.9500 . ? C22 C23 1.390(5) . ? C22 C25 1.473(5) . ? C23 C24 1.374(5) . ? C23 H12 0.9500 . ? C24 H13 0.9500 . ? C25 F5 1.333(4) . ? C25 F4 1.334(4) . ? C25 F6 1.342(4) . ? C26 C31 1.396(5) . ? C26 C27 1.401(5) . ? C27 C28 1.381(5) . ? C27 H14 0.9500 . ? C28 C29 1.385(5) . ? C28 H15 0.9500 . ? C29 O2 1.367(4) . ? C29 C30 1.402(5) . ? C30 C31 1.372(5) . ? C30 H16 0.9500 . ? C31 H17 0.9500 . ? O2 C32 1.437(4) . ? C32 H18 0.9800 . ? C32 H19 0.9800 . ? C32 H20 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C1 C19 127.9(3) . . ? C16 C1 C2 106.6(3) . . ? C19 C1 C2 125.4(3) . . ? C3 C2 C7 121.3(3) . . ? C3 C2 C1 129.2(3) . . ? C7 C2 C1 109.4(3) . . ? C2 C3 C4 118.2(3) . . ? C2 C3 H1 120.9 . . ? C4 C3 H1 120.9 . . ? C5 C4 O1 124.7(3) . . ? C5 C4 C3 121.4(3) . . ? O1 C4 C3 113.9(3) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H2 119.8 . . ? C6 C5 H2 119.8 . . ? C7 C6 C5 119.3(3) . . ? C7 C6 H3 120.4 . . ? C5 C6 H3 120.4 . . ? C6 C7 C2 119.5(3) . . ? C6 C7 C8 134.4(3) . . ? C2 C7 C8 106.1(3) . . ? C9 C8 C16 110.4(3) . . ? C9 C8 C7 142.8(3) . . ? C16 C8 C7 106.8(3) . . ? C8 C9 C26 129.5(3) . . ? C8 C9 C10 106.3(3) . . ? C26 C9 C10 124.1(3) . . ? C11 C10 C15 119.7(3) . . ? C11 C10 C9 130.6(3) . . ? C15 C10 C9 109.6(3) . . ? C10 C11 C12 118.1(3) . . ? C10 C11 H4 120.9 . . ? C12 C11 H4 120.9 . . ? C13 C12 C11 121.9(3) . . ? C13 C12 C18 120.2(3) . . ? C11 C12 C18 117.8(3) . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H5 119.9 . . ? C14 C13 H5 119.9 . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H6 120.5 . . ? C13 C14 H6 120.5 . . ? C14 C15 C10 120.9(3) . . ? C14 C15 C16 133.3(3) . . ? C10 C15 C16 105.7(3) . . ? C1 C16 C8 111.0(3) . . ? C1 C16 C15 140.9(3) . . ? C8 C16 C15 108.0(3) . . ? C4 O1 C17 117.5(3) . . ? O1 C17 H7 109.5 . . ? O1 C17 H8 109.5 . . ? H7 C17 H8 109.5 . . ? O1 C17 H9 109.5 . . ? H7 C17 H9 109.5 . . ? H8 C17 H9 109.5 . . ? F2 C18 F3 106.2(3) . . ? F2 C18 F1 105.8(3) . . ? F3 C18 F1 105.7(3) . . ? F2 C18 C12 113.2(3) . . ? F3 C18 C12 112.5(3) . . ? F1 C18 C12 112.8(3) . . ? C20 C19 C24 118.0(3) . . ? C20 C19 C1 120.4(3) . . ? C24 C19 C1 121.6(3) . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H10 119.8 . . ? C19 C20 H10 119.8 . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H11 119.7 . . ? C20 C21 H11 119.7 . . ? C21 C22 C23 119.7(3) . . ? C21 C22 C25 121.6(3) . . ? C23 C22 C25 118.7(3) . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H12 119.9 . . ? C22 C23 H12 119.9 . . ? C23 C24 C19 121.0(3) . . ? C23 C24 H13 119.5 . . ? C19 C24 H13 119.5 . . ? F5 C25 F4 105.0(3) . . ? F5 C25 F6 104.8(3) . . ? F4 C25 F6 105.6(3) . . ? F5 C25 C22 113.3(3) . . ? F4 C25 C22 113.8(3) . . ? F6 C25 C22 113.6(3) . . ? C31 C26 C27 117.1(3) . . ? C31 C26 C9 121.6(3) . . ? C27 C26 C9 121.3(3) . . ? C28 C27 C26 122.2(3) . . ? C28 C27 H14 118.9 . . ? C26 C27 H14 118.9 . . ? C27 C28 C29 119.5(3) . . ? C27 C28 H15 120.3 . . ? C29 C28 H15 120.3 . . ? O2 C29 C28 125.5(3) . . ? O2 C29 C30 114.9(3) . . ? C28 C29 C30 119.5(3) . . ? C31 C30 C29 120.1(3) . . ? C31 C30 H16 119.9 . . ? C29 C30 H16 119.9 . . ? C30 C31 C26 121.6(3) . . ? C30 C31 H17 119.2 . . ? C26 C31 H17 119.2 . . ? C29 O2 C32 117.0(3) . . ? O2 C32 H18 109.5 . . ? O2 C32 H19 109.5 . . ? H18 C32 H19 109.5 . . ? O2 C32 H20 109.5 . . ? H18 C32 H20 109.5 . . ? H19 C32 H20 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C1 C2 C3 176.2(3) . . . . ? C19 C1 C2 C3 -4.0(5) . . . . ? C16 C1 C2 C7 0.0(4) . . . . ? C19 C1 C2 C7 179.9(3) . . . . ? C7 C2 C3 C4 -0.6(5) . . . . ? C1 C2 C3 C4 -176.3(3) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C2 C3 C4 O1 -178.7(3) . . . . ? O1 C4 C5 C6 179.4(3) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C4 C5 C6 C7 -0.9(5) . . . . ? C5 C6 C7 C2 0.9(5) . . . . ? C5 C6 C7 C8 177.2(3) . . . . ? C3 C2 C7 C6 -0.2(5) . . . . ? C1 C2 C7 C6 176.3(3) . . . . ? C3 C2 C7 C8 -177.4(3) . . . . ? C1 C2 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 5.0(7) . . . . ? C2 C7 C8 C9 -178.3(4) . . . . ? C6 C7 C8 C16 -175.2(3) . . . . ? C2 C7 C8 C16 1.5(3) . . . . ? C16 C8 C9 C26 -179.5(3) . . . . ? C7 C8 C9 C26 0.3(7) . . . . ? C16 C8 C9 C10 -0.9(4) . . . . ? C7 C8 C9 C10 178.8(4) . . . . ? C8 C9 C10 C11 -175.4(3) . . . . ? C26 C9 C10 C11 3.3(5) . . . . ? C8 C9 C10 C15 1.0(4) . . . . ? C26 C9 C10 C15 179.7(3) . . . . ? C15 C10 C11 C12 1.8(5) . . . . ? C9 C10 C11 C12 178.0(3) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? C10 C11 C12 C18 -179.8(3) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C18 C12 C13 C14 178.3(3) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C10 -0.1(5) . . . . ? C13 C14 C15 C16 -176.9(3) . . . . ? C11 C10 C15 C14 -1.4(5) . . . . ? C9 C10 C15 C14 -178.3(3) . . . . ? C11 C10 C15 C16 176.2(3) . . . . ? C9 C10 C15 C16 -0.7(4) . . . . ? C19 C1 C16 C8 -178.9(3) . . . . ? C2 C1 C16 C8 0.9(4) . . . . ? C19 C1 C16 C15 -2.3(7) . . . . ? C2 C1 C16 C15 177.6(4) . . . . ? C9 C8 C16 C1 178.3(3) . . . . ? C7 C8 C16 C1 -1.5(4) . . . . ? C9 C8 C16 C15 0.5(4) . . . . ? C7 C8 C16 C15 -179.3(2) . . . . ? C14 C15 C16 C1 0.6(7) . . . . ? C10 C15 C16 C1 -176.6(4) . . . . ? C14 C15 C16 C8 177.3(3) . . . . ? C10 C15 C16 C8 0.1(3) . . . . ? C5 C4 O1 C17 3.4(5) . . . . ? C3 C4 O1 C17 -177.3(3) . . . . ? C13 C12 C18 F2 121.8(3) . . . . ? C11 C12 C18 F2 -59.2(4) . . . . ? C13 C12 C18 F3 -117.8(3) . . . . ? C11 C12 C18 F3 61.2(4) . . . . ? C13 C12 C18 F1 1.7(5) . . . . ? C11 C12 C18 F1 -179.3(3) . . . . ? C16 C1 C19 C20 130.9(4) . . . . ? C2 C1 C19 C20 -49.0(5) . . . . ? C16 C1 C19 C24 -47.9(5) . . . . ? C2 C1 C19 C24 132.3(3) . . . . ? C24 C19 C20 C21 1.0(5) . . . . ? C1 C19 C20 C21 -177.8(3) . . . . ? C19 C20 C21 C22 -0.4(5) . . . . ? C20 C21 C22 C23 -0.4(5) . . . . ? C20 C21 C22 C25 179.7(3) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? C25 C22 C23 C24 -179.5(3) . . . . ? C22 C23 C24 C19 0.0(5) . . . . ? C20 C19 C24 C23 -0.7(5) . . . . ? C1 C19 C24 C23 178.0(3) . . . . ? C21 C22 C25 F5 115.5(4) . . . . ? C23 C22 C25 F5 -64.4(4) . . . . ? C21 C22 C25 F4 -4.2(5) . . . . ? C23 C22 C25 F4 175.9(3) . . . . ? C21 C22 C25 F6 -125.1(4) . . . . ? C23 C22 C25 F6 55.0(4) . . . . ? C8 C9 C26 C31 -139.7(4) . . . . ? C10 C9 C26 C31 42.0(5) . . . . ? C8 C9 C26 C27 39.2(5) . . . . ? C10 C9 C26 C27 -139.2(3) . . . . ? C31 C26 C27 C28 -0.2(5) . . . . ? C9 C26 C27 C28 -179.1(3) . . . . ? C26 C27 C28 C29 0.9(5) . . . . ? C27 C28 C29 O2 177.4(3) . . . . ? C27 C28 C29 C30 -1.2(5) . . . . ? O2 C29 C30 C31 -177.9(3) . . . . ? C28 C29 C30 C31 0.8(5) . . . . ? C29 C30 C31 C26 -0.1(5) . . . . ? C27 C26 C31 C30 -0.2(5) . . . . ? C9 C26 C31 C30 178.7(3) . . . . ? C28 C29 O2 C32 1.8(5) . . . . ? C30 C29 O2 C32 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.331 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.081 data_3 _database_code_depnum_ccdc_archive 'CCDC 917512' #TrackingRef '2a_2b_2d_2f_2bd_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 O2' _chemical_formula_weight 440.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.094(6) _cell_length_b 12.055(7) _cell_length_c 19.805(11) _cell_angle_alpha 81.395(20) _cell_angle_beta 80.70(2) _cell_angle_gamma 89.36(2) _cell_volume 2351(2) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 2888 _cell_measurement_theta_min 3.0277 _cell_measurement_theta_max 25.3230 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.0100 _exptl_crystal_size_min 0.0010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6992 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12467 _diffrn_reflns_av_R_equivalents 0.0968 _diffrn_reflns_av_sigmaI/netI 0.2706 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8052 _reflns_number_gt 2554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1504P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8052 _refine_ls_number_parameters 615 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2815 _refine_ls_R_factor_gt 0.1334 _refine_ls_wR_factor_ref 0.4027 _refine_ls_wR_factor_gt 0.3020 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2024(15) 0.7927(9) 0.4759(5) 0.081(4) Uani 1 1 d . . . H1 H 0.2869 0.7594 0.4572 0.122 Uiso 1 1 calc R . . H2 H 0.2216 0.8625 0.4926 0.122 Uiso 1 1 calc R . . H3 H 0.1467 0.8090 0.4396 0.122 Uiso 1 1 calc R . . O1 O 0.1322(8) 0.7155(5) 0.5323(3) 0.061(2) Uani 1 1 d . . . C2 C 0.1355(9) 0.6061(8) 0.5251(4) 0.035(2) Uani 1 1 d . . . O2 O 0.1869(7) 0.5740(5) 0.4716(3) 0.0477(18) Uani 1 1 d . . . C3 C 0.0792(10) 0.5326(8) 0.5882(4) 0.038(2) Uani 1 1 d . . . H4 H 0.0862 0.4537 0.5897 0.046 Uiso 1 1 calc R . . C4 C 0.0163(10) 0.5746(7) 0.6456(4) 0.036(2) Uani 1 1 d . . . H5 H 0.0075 0.6536 0.6430 0.043 Uiso 1 1 calc R . . C5 C -0.0375(9) 0.5043(7) 0.7102(4) 0.029(2) Uani 1 1 d . . . C6 C -0.1056(9) 0.5481(7) 0.7656(4) 0.033(2) Uani 1 1 d . . . C7 C -0.1221(9) 0.6669(7) 0.7760(4) 0.031(2) Uani 1 1 d . . . C8 C -0.1990(9) 0.6727(7) 0.8392(4) 0.030(2) Uani 1 1 d . . . C9 C -0.2379(10) 0.5568(7) 0.8738(4) 0.034(2) Uani 1 1 d . . . C10 C -0.3175(9) 0.5219(8) 0.9380(4) 0.034(2) Uani 1 1 d . . . H6 H -0.3533 0.5733 0.9680 0.041 Uiso 1 1 calc R . . C11 C -0.3409(9) 0.4069(7) 0.9549(4) 0.036(2) Uani 1 1 d . . . H7 H -0.3931 0.3794 0.9985 0.043 Uiso 1 1 calc R . . C12 C -0.2923(9) 0.3312(8) 0.9121(4) 0.037(2) Uani 1 1 d . . . H8 H -0.3134 0.2536 0.9254 0.045 Uiso 1 1 calc R . . C13 C -0.2123(9) 0.3687(7) 0.8492(4) 0.032(2) Uani 1 1 d . . . H9 H -0.1774 0.3164 0.8196 0.038 Uiso 1 1 calc R . . C14 C -0.1829(9) 0.4819(7) 0.8293(4) 0.028(2) Uani 1 1 d . . . C15 C -0.0084(10) 0.3829(8) 0.7166(4) 0.037(2) Uani 1 1 d . . . C16 C 0.0849(9) 0.3394(7) 0.7584(4) 0.032(2) Uani 1 1 d . . . H10 H 0.1327 0.3887 0.7793 0.039 Uiso 1 1 calc R . . C17 C 0.1081(11) 0.2256(8) 0.7695(5) 0.047(3) Uani 1 1 d . . . H11 H 0.1719 0.1979 0.7981 0.057 Uiso 1 1 calc R . . C18 C 0.0415(10) 0.1517(8) 0.7404(5) 0.044(3) Uani 1 1 d . . . H12 H 0.0586 0.0736 0.7485 0.052 Uiso 1 1 calc R . . C19 C -0.0507(12) 0.1928(8) 0.6991(5) 0.052(3) Uani 1 1 d . . . H13 H -0.0986 0.1418 0.6794 0.062 Uiso 1 1 calc R . . C20 C -0.0764(11) 0.3093(8) 0.6852(5) 0.043(3) Uani 1 1 d . . . H14 H -0.1380 0.3367 0.6553 0.052 Uiso 1 1 calc R . . C21 C -0.0671(9) 0.7682(7) 0.7253(4) 0.031(2) Uani 1 1 d . . . C22 C -0.1504(9) 0.8285(7) 0.6838(4) 0.038(2) Uani 1 1 d . . . H15 H -0.2430 0.8090 0.6904 0.045 Uiso 1 1 calc R . . C23 C -0.1010(9) 0.9153(7) 0.6335(4) 0.039(2) Uani 1 1 d . . . H16 H -0.1595 0.9553 0.6057 0.046 Uiso 1 1 calc R . . C24 C 0.0330(9) 0.9451(7) 0.6230(4) 0.036(2) Uani 1 1 d . . . H17 H 0.0674 1.0049 0.5879 0.043 Uiso 1 1 calc R . . C25 C 0.1179(10) 0.8860(8) 0.6648(5) 0.042(3) Uani 1 1 d . . . H18 H 0.2104 0.9058 0.6583 0.051 Uiso 1 1 calc R . . C26 C 0.0666(9) 0.7990(8) 0.7152(4) 0.033(2) Uani 1 1 d . . . H19 H 0.1244 0.7595 0.7436 0.039 Uiso 1 1 calc R . . C27 C -0.2413(9) 0.7752(7) 0.8692(4) 0.032(2) Uani 1 1 d . . . C28 C -0.1513(10) 0.8628(7) 0.8712(4) 0.035(2) Uani 1 1 d . . . H20 H -0.0601 0.8586 0.8503 0.043 Uiso 1 1 calc R . . C29 C -0.1927(11) 0.9548(8) 0.9029(5) 0.045(3) Uani 1 1 d . . . H21 H -0.1302 1.0118 0.9053 0.054 Uiso 1 1 calc R . . C30 C -0.3318(12) 0.9629(9) 0.9322(5) 0.056(3) Uani 1 1 d . . . H22 H -0.3626 1.0256 0.9540 0.067 Uiso 1 1 calc R . . C31 C -0.4195(11) 0.8786(8) 0.9282(4) 0.040(2) Uani 1 1 d . . . H23 H -0.5119 0.8853 0.9461 0.048 Uiso 1 1 calc R . . C32 C -0.3776(9) 0.7845(7) 0.8989(4) 0.037(2) Uani 1 1 d . . . H24 H -0.4401 0.7262 0.8987 0.044 Uiso 1 1 calc R . . C33 C -0.2915(15) 0.7204(9) 0.4749(5) 0.076(4) Uani 1 1 d . . . H25 H -0.3462 0.7230 0.4381 0.114 Uiso 1 1 calc R . . H26 H -0.2719 0.6421 0.4914 0.114 Uiso 1 1 calc R . . H27 H -0.2072 0.7619 0.4569 0.114 Uiso 1 1 calc R . . O3 O -0.3634(8) 0.7699(5) 0.5309(3) 0.062(2) Uani 1 1 d . . . C34 C -0.3610(10) 0.8816(8) 0.5240(5) 0.041(2) Uani 1 1 d . . . O4 O -0.3096(7) 0.9412(5) 0.4710(3) 0.0493(19) Uani 1 1 d . . . C35 C -0.4213(8) 0.9260(7) 0.5879(4) 0.028(2) Uani 1 1 d . . . H28 H -0.4151 1.0042 0.5894 0.034 Uiso 1 1 calc R . . C36 C -0.4847(9) 0.8581(7) 0.6436(4) 0.032(2) Uani 1 1 d . . . H29 H -0.4970 0.7815 0.6397 0.039 Uiso 1 1 calc R . . C37 C -0.5358(9) 0.8953(8) 0.7100(4) 0.036(2) Uani 1 1 d . . . C38 C -0.6020(9) 0.8246(7) 0.7645(4) 0.028(2) Uani 1 1 d . . . C39 C -0.6192(9) 0.7021(7) 0.7740(4) 0.031(2) Uani 1 1 d . . . C40 C -0.7013(9) 0.6636(7) 0.8377(4) 0.028(2) Uani 1 1 d . . . C41 C -0.7423(9) 0.7628(7) 0.8706(4) 0.032(2) Uani 1 1 d . . . C42 C -0.8215(9) 0.7707(8) 0.9324(4) 0.034(2) Uani 1 1 d . . . H30 H -0.8581 0.7046 0.9615 0.041 Uiso 1 1 calc R . . C43 C -0.8489(9) 0.8752(8) 0.9531(5) 0.038(2) Uani 1 1 d . . . H31 H -0.9043 0.8805 0.9961 0.046 Uiso 1 1 calc R . . C44 C -0.7949(10) 0.9716(8) 0.9107(4) 0.039(2) Uani 1 1 d . . . H32 H -0.8160 1.0430 0.9240 0.047 Uiso 1 1 calc R . . C45 C -0.7096(9) 0.9640(7) 0.8485(4) 0.037(2) Uani 1 1 d . . . H33 H -0.6710 1.0301 0.8203 0.044 Uiso 1 1 calc R . . C46 C -0.6817(8) 0.8616(7) 0.8283(4) 0.027(2) Uani 1 1 d . . . C47 C -0.5091(9) 1.0136(7) 0.7159(4) 0.031(2) Uani 1 1 d . . . C48 C -0.5765(10) 1.1025(7) 0.6852(5) 0.038(2) Uani 1 1 d . . . H34 H -0.6386 1.0890 0.6559 0.046 Uiso 1 1 calc R . . C49 C -0.5548(12) 1.2121(8) 0.6965(5) 0.050(3) Uani 1 1 d . . . H35 H -0.6036 1.2725 0.6763 0.060 Uiso 1 1 calc R . . C50 C -0.4600(11) 1.2316(9) 0.7380(5) 0.051(3) Uani 1 1 d . . . H36 H -0.4418 1.3057 0.7451 0.061 Uiso 1 1 calc R . . C51 C -0.3944(11) 1.1430(9) 0.7679(5) 0.051(3) Uani 1 1 d . . . H37 H -0.3327 1.1565 0.7974 0.061 Uiso 1 1 calc R . . C52 C -0.4140(10) 1.0342(7) 0.7571(4) 0.038(2) Uani 1 1 d . . . H38 H -0.3641 0.9744 0.7773 0.046 Uiso 1 1 calc R . . C53 C -0.5630(9) 0.6248(7) 0.7236(4) 0.029(2) Uani 1 1 d . . . C54 C -0.6483(9) 0.5856(7) 0.6836(4) 0.040(2) Uani 1 1 d . . . H39 H -0.7411 0.6030 0.6911 0.047 Uiso 1 1 calc R . . C55 C -0.5979(10) 0.5204(7) 0.6321(5) 0.040(2) Uani 1 1 d . . . H40 H -0.6560 0.4934 0.6048 0.048 Uiso 1 1 calc R . . C56 C -0.4627(9) 0.4961(7) 0.6220(4) 0.035(2) Uani 1 1 d . . . H41 H -0.4277 0.4530 0.5869 0.042 Uiso 1 1 calc R . . C57 C -0.3776(10) 0.5335(7) 0.6621(4) 0.041(3) Uani 1 1 d . . . H42 H -0.2848 0.5165 0.6548 0.049 Uiso 1 1 calc R . . C58 C -0.4310(9) 0.5974(7) 0.7139(4) 0.035(2) Uani 1 1 d . . . H43 H -0.3737 0.6218 0.7426 0.042 Uiso 1 1 calc R . . C59 C -0.7397(9) 0.5481(7) 0.8692(4) 0.029(2) Uani 1 1 d . . . C60 C -0.8743(10) 0.5228(9) 0.8953(4) 0.045(3) Uani 1 1 d . . . H44 H -0.9400 0.5794 0.8910 0.054 Uiso 1 1 calc R . . C61 C -0.9137(11) 0.4124(8) 0.9282(4) 0.045(3) Uani 1 1 d . . . H45 H -1.0048 0.3948 0.9474 0.054 Uiso 1 1 calc R . . C62 C -0.8179(10) 0.3327(8) 0.9317(4) 0.042(2) Uani 1 1 d . . . H46 H -0.8429 0.2592 0.9547 0.050 Uiso 1 1 calc R . . C63 C -0.6839(10) 0.3555(7) 0.9025(5) 0.042(2) Uani 1 1 d . . . H47 H -0.6187 0.2981 0.9045 0.051 Uiso 1 1 calc R . . C64 C -0.6484(11) 0.4615(7) 0.8710(4) 0.039(2) Uani 1 1 d . . . H48 H -0.5580 0.4767 0.8495 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.152(14) 0.044(7) 0.030(6) 0.009(5) 0.028(7) -0.027(7) O1 0.106(7) 0.039(4) 0.027(4) 0.003(3) 0.016(4) -0.011(4) C2 0.037(6) 0.034(5) 0.031(5) -0.007(4) 0.001(4) 0.007(4) O2 0.061(5) 0.049(4) 0.028(4) -0.008(3) 0.012(3) -0.001(4) C3 0.045(6) 0.036(5) 0.031(5) -0.009(4) 0.004(4) -0.009(5) C4 0.050(6) 0.031(5) 0.024(5) 0.000(4) -0.003(4) -0.003(4) C5 0.033(5) 0.029(5) 0.020(4) 0.001(4) 0.001(4) 0.003(4) C6 0.027(5) 0.040(5) 0.026(5) 0.001(4) 0.004(4) 0.002(4) C7 0.033(5) 0.035(5) 0.021(5) -0.001(4) -0.001(4) -0.005(4) C8 0.026(5) 0.039(5) 0.021(4) -0.001(4) 0.003(4) 0.006(4) C9 0.046(6) 0.027(5) 0.024(5) 0.004(4) -0.001(4) -0.011(4) C10 0.022(5) 0.045(6) 0.031(5) -0.005(4) 0.008(4) -0.002(4) C11 0.039(6) 0.034(5) 0.027(5) 0.010(4) 0.010(4) -0.001(4) C12 0.031(5) 0.039(6) 0.034(5) 0.009(4) 0.009(4) -0.022(4) C13 0.033(5) 0.040(5) 0.021(4) -0.002(4) 0.000(4) -0.004(4) C14 0.038(6) 0.021(5) 0.022(4) -0.001(4) 0.003(4) -0.001(4) C15 0.041(6) 0.044(6) 0.020(5) -0.004(4) 0.017(4) -0.001(5) C16 0.035(5) 0.029(5) 0.027(5) -0.002(4) 0.012(4) -0.002(4) C17 0.057(7) 0.045(6) 0.034(5) 0.002(5) 0.002(5) 0.011(6) C18 0.051(7) 0.040(6) 0.035(5) -0.008(5) 0.009(5) -0.003(5) C19 0.073(8) 0.035(6) 0.044(6) -0.009(5) 0.002(6) 0.002(6) C20 0.061(7) 0.036(6) 0.028(5) -0.013(4) 0.015(5) -0.007(5) C21 0.038(6) 0.027(5) 0.025(5) 0.001(4) -0.002(4) 0.005(4) C22 0.021(5) 0.043(6) 0.042(5) 0.011(4) 0.000(4) -0.005(4) C23 0.033(6) 0.037(6) 0.037(5) 0.015(4) 0.002(4) 0.002(4) C24 0.028(5) 0.035(5) 0.037(5) -0.002(4) 0.012(4) -0.001(4) C25 0.026(5) 0.047(6) 0.044(6) -0.002(5) 0.019(4) -0.003(5) C26 0.024(5) 0.046(6) 0.024(5) 0.000(4) 0.002(4) -0.005(4) C27 0.031(5) 0.036(5) 0.025(5) 0.002(4) 0.003(4) 0.009(4) C28 0.034(6) 0.043(6) 0.025(5) -0.005(4) 0.011(4) -0.015(4) C29 0.056(7) 0.030(5) 0.048(6) -0.011(4) -0.003(5) -0.004(5) C30 0.069(9) 0.050(7) 0.047(6) -0.010(5) 0.001(6) 0.009(6) C31 0.045(6) 0.045(6) 0.029(5) -0.015(4) 0.002(4) 0.009(5) C32 0.038(6) 0.039(6) 0.027(5) 0.009(4) 0.000(4) 0.013(5) C33 0.132(13) 0.053(7) 0.030(6) 0.000(5) 0.020(7) -0.001(8) O3 0.114(7) 0.036(4) 0.025(3) -0.006(3) 0.025(4) 0.007(4) C34 0.055(7) 0.034(6) 0.029(5) -0.002(4) 0.008(5) -0.004(5) O4 0.070(5) 0.041(4) 0.028(3) 0.002(3) 0.013(3) -0.009(4) C35 0.023(5) 0.036(5) 0.022(4) 0.002(4) 0.006(4) -0.009(4) C36 0.043(6) 0.035(5) 0.016(4) -0.001(4) -0.002(4) 0.001(4) C37 0.029(6) 0.045(6) 0.029(5) -0.002(4) 0.007(4) -0.003(5) C38 0.029(5) 0.028(5) 0.021(4) 0.003(4) 0.010(4) -0.003(4) C39 0.038(6) 0.027(5) 0.024(5) -0.003(4) 0.011(4) 0.002(4) C40 0.032(5) 0.028(5) 0.021(4) -0.005(4) 0.004(4) 0.001(4) C41 0.031(5) 0.039(5) 0.017(4) 0.003(4) 0.013(4) -0.008(4) C42 0.026(5) 0.045(6) 0.025(5) 0.004(4) 0.004(4) 0.002(4) C43 0.035(6) 0.045(6) 0.031(5) -0.001(4) -0.001(4) -0.003(5) C44 0.040(6) 0.039(6) 0.035(5) -0.003(4) 0.002(4) 0.004(5) C45 0.044(6) 0.033(5) 0.032(5) -0.001(4) -0.004(4) -0.001(5) C46 0.016(5) 0.037(5) 0.024(4) 0.003(4) 0.005(4) -0.008(4) C47 0.033(5) 0.035(5) 0.019(4) 0.001(4) 0.005(4) 0.004(4) C48 0.037(6) 0.032(5) 0.038(5) 0.004(4) 0.007(4) -0.004(4) C49 0.059(8) 0.028(6) 0.053(6) 0.002(5) 0.016(6) -0.008(5) C50 0.060(8) 0.040(6) 0.047(6) -0.003(5) 0.000(6) 0.001(6) C51 0.059(7) 0.049(7) 0.041(6) -0.008(5) 0.004(5) -0.003(6) C52 0.053(7) 0.028(5) 0.024(5) 0.005(4) 0.016(4) -0.006(5) C53 0.032(6) 0.036(5) 0.015(4) 0.010(4) -0.005(4) -0.001(4) C54 0.026(5) 0.042(6) 0.042(6) 0.002(4) 0.009(4) 0.003(5) C55 0.033(6) 0.037(6) 0.052(6) -0.011(5) -0.005(5) -0.001(5) C56 0.038(6) 0.037(5) 0.026(5) 0.001(4) -0.001(4) -0.007(4) C57 0.036(6) 0.041(6) 0.036(5) 0.000(4) 0.017(4) 0.008(5) C58 0.029(5) 0.043(6) 0.030(5) 0.007(4) -0.003(4) -0.003(4) C59 0.038(6) 0.029(5) 0.014(4) 0.000(3) 0.014(4) -0.010(4) C60 0.047(7) 0.067(7) 0.016(5) -0.003(5) 0.009(4) 0.002(5) C61 0.047(7) 0.058(7) 0.024(5) 0.008(5) 0.003(4) -0.014(5) C62 0.055(7) 0.041(6) 0.021(5) 0.012(4) 0.003(4) -0.014(5) C63 0.050(7) 0.026(5) 0.043(6) -0.002(4) 0.012(5) -0.016(5) C64 0.061(7) 0.036(6) 0.017(4) 0.004(4) 0.001(4) -0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.436(12) . ? C1 H1 0.9800 . ? C1 H2 0.9800 . ? C1 H3 0.9800 . ? O1 C2 1.347(10) . ? C2 O2 1.218(10) . ? C2 C3 1.456(12) . ? C3 C4 1.372(11) . ? C3 H4 0.9500 . ? C4 C5 1.452(11) . ? C4 H5 0.9500 . ? C5 C6 1.370(11) . ? C5 C15 1.480(11) . ? C6 C7 1.481(11) . ? C6 C14 1.494(11) . ? C7 C8 1.373(11) . ? C7 C21 1.508(12) . ? C8 C27 1.480(11) . ? C8 C9 1.488(12) . ? C9 C10 1.399(11) . ? C9 C14 1.404(11) . ? C10 C11 1.390(12) . ? C10 H6 0.9500 . ? C11 C12 1.373(12) . ? C11 H7 0.9500 . ? C12 C13 1.387(11) . ? C12 H8 0.9500 . ? C13 C14 1.384(11) . ? C13 H9 0.9500 . ? C15 C16 1.399(12) . ? C15 C20 1.400(13) . ? C16 C17 1.380(11) . ? C16 H10 0.9500 . ? C17 C18 1.368(14) . ? C17 H11 0.9500 . ? C18 C19 1.377(13) . ? C18 H12 0.9500 . ? C19 C20 1.420(12) . ? C19 H13 0.9500 . ? C20 H14 0.9500 . ? C21 C26 1.379(13) . ? C21 C22 1.394(11) . ? C22 C23 1.369(12) . ? C22 H15 0.9500 . ? C23 C24 1.378(13) . ? C23 H16 0.9500 . ? C24 C25 1.402(12) . ? C24 H17 0.9500 . ? C25 C26 1.377(12) . ? C25 H18 0.9500 . ? C26 H19 0.9500 . ? C27 C28 1.410(12) . ? C27 C32 1.417(12) . ? C28 C29 1.383(11) . ? C28 H20 0.9500 . ? C29 C30 1.438(14) . ? C29 H21 0.9500 . ? C30 C31 1.375(14) . ? C30 H22 0.9500 . ? C31 C32 1.382(11) . ? C31 H23 0.9500 . ? C32 H24 0.9500 . ? C33 O3 1.428(11) . ? C33 H25 0.9800 . ? C33 H26 0.9800 . ? C33 H27 0.9800 . ? O3 C34 1.333(10) . ? C34 O4 1.222(10) . ? C34 C35 1.485(12) . ? C35 C36 1.345(11) . ? C35 H28 0.9500 . ? C36 C37 1.466(11) . ? C36 H29 0.9500 . ? C37 C38 1.356(12) . ? C37 C47 1.479(12) . ? C38 C39 1.470(11) . ? C38 C46 1.509(11) . ? C39 C40 1.411(11) . ? C39 C53 1.505(11) . ? C40 C59 1.467(11) . ? C40 C41 1.470(11) . ? C41 C42 1.365(11) . ? C41 C46 1.431(11) . ? C42 C43 1.394(12) . ? C42 H30 0.9500 . ? C43 C44 1.387(13) . ? C43 H31 0.9500 . ? C44 C45 1.399(12) . ? C44 H32 0.9500 . ? C45 C46 1.366(11) . ? C45 H33 0.9500 . ? C47 C48 1.380(11) . ? C47 C52 1.403(13) . ? C48 C49 1.398(13) . ? C48 H34 0.9500 . ? C49 C50 1.401(15) . ? C49 H35 0.9500 . ? C50 C51 1.361(13) . ? C50 H36 0.9500 . ? C51 C52 1.382(13) . ? C51 H37 0.9500 . ? C52 H38 0.9500 . ? C53 C58 1.360(12) . ? C53 C54 1.390(13) . ? C54 C55 1.408(12) . ? C54 H39 0.9500 . ? C55 C56 1.382(12) . ? C55 H40 0.9500 . ? C56 C57 1.380(13) . ? C56 H41 0.9500 . ? C57 C58 1.410(12) . ? C57 H42 0.9500 . ? C58 H43 0.9500 . ? C59 C64 1.385(11) . ? C59 C60 1.394(13) . ? C60 C61 1.422(13) . ? C60 H44 0.9500 . ? C61 C62 1.358(12) . ? C61 H45 0.9500 . ? C62 C63 1.396(13) . ? C62 H46 0.9500 . ? C63 C64 1.361(11) . ? C63 H47 0.9500 . ? C64 H48 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1 109.5 . . ? O1 C1 H2 109.5 . . ? H1 C1 H2 109.5 . . ? O1 C1 H3 109.5 . . ? H1 C1 H3 109.5 . . ? H2 C1 H3 109.5 . . ? C2 O1 C1 117.0(8) . . ? O2 C2 O1 122.1(8) . . ? O2 C2 C3 124.7(8) . . ? O1 C2 C3 113.2(7) . . ? C4 C3 C2 121.6(8) . . ? C4 C3 H4 119.2 . . ? C2 C3 H4 119.2 . . ? C3 C4 C5 123.3(8) . . ? C3 C4 H5 118.3 . . ? C5 C4 H5 118.3 . . ? C6 C5 C4 122.0(8) . . ? C6 C5 C15 120.0(7) . . ? C4 C5 C15 117.8(7) . . ? C5 C6 C7 129.3(8) . . ? C5 C6 C14 125.5(8) . . ? C7 C6 C14 105.2(7) . . ? C8 C7 C6 109.7(7) . . ? C8 C7 C21 124.0(8) . . ? C6 C7 C21 126.3(7) . . ? C7 C8 C27 127.1(8) . . ? C7 C8 C9 108.8(7) . . ? C27 C8 C9 124.1(7) . . ? C10 C9 C14 123.0(8) . . ? C10 C9 C8 129.0(8) . . ? C14 C9 C8 108.0(7) . . ? C11 C10 C9 115.4(8) . . ? C11 C10 H6 122.3 . . ? C9 C10 H6 122.3 . . ? C12 C11 C10 123.4(8) . . ? C12 C11 H7 118.3 . . ? C10 C11 H7 118.3 . . ? C11 C12 C13 119.5(8) . . ? C11 C12 H8 120.2 . . ? C13 C12 H8 120.2 . . ? C14 C13 C12 120.3(8) . . ? C14 C13 H9 119.8 . . ? C12 C13 H9 119.8 . . ? C13 C14 C9 118.2(8) . . ? C13 C14 C6 133.3(7) . . ? C9 C14 C6 108.4(7) . . ? C16 C15 C20 119.0(9) . . ? C16 C15 C5 118.8(9) . . ? C20 C15 C5 122.1(8) . . ? C17 C16 C15 120.6(9) . . ? C17 C16 H10 119.7 . . ? C15 C16 H10 119.7 . . ? C18 C17 C16 121.6(9) . . ? C18 C17 H11 119.2 . . ? C16 C17 H11 119.2 . . ? C17 C18 C19 118.6(9) . . ? C17 C18 H12 120.7 . . ? C19 C18 H12 120.7 . . ? C18 C19 C20 121.8(11) . . ? C18 C19 H13 119.1 . . ? C20 C19 H13 119.1 . . ? C15 C20 C19 118.3(9) . . ? C15 C20 H14 120.9 . . ? C19 C20 H14 120.9 . . ? C26 C21 C22 118.3(8) . . ? C26 C21 C7 121.8(7) . . ? C22 C21 C7 119.7(9) . . ? C23 C22 C21 121.2(9) . . ? C23 C22 H15 119.4 . . ? C21 C22 H15 119.4 . . ? C22 C23 C24 120.4(8) . . ? C22 C23 H16 119.8 . . ? C24 C23 H16 119.8 . . ? C23 C24 C25 119.2(9) . . ? C23 C24 H17 120.4 . . ? C25 C24 H17 120.4 . . ? C26 C25 C24 119.7(9) . . ? C26 C25 H18 120.2 . . ? C24 C25 H18 120.2 . . ? C25 C26 C21 121.2(8) . . ? C25 C26 H19 119.4 . . ? C21 C26 H19 119.4 . . ? C28 C27 C32 118.5(8) . . ? C28 C27 C8 123.0(8) . . ? C32 C27 C8 118.5(9) . . ? C29 C28 C27 121.5(9) . . ? C29 C28 H20 119.3 . . ? C27 C28 H20 119.3 . . ? C28 C29 C30 119.1(10) . . ? C28 C29 H21 120.5 . . ? C30 C29 H21 120.5 . . ? C31 C30 C29 118.9(9) . . ? C31 C30 H22 120.5 . . ? C29 C30 H22 120.5 . . ? C30 C31 C32 122.2(10) . . ? C30 C31 H23 118.9 . . ? C32 C31 H23 118.9 . . ? C31 C32 C27 119.8(10) . . ? C31 C32 H24 120.1 . . ? C27 C32 H24 120.1 . . ? O3 C33 H25 109.5 . . ? O3 C33 H26 109.5 . . ? H25 C33 H26 109.5 . . ? O3 C33 H27 109.5 . . ? H25 C33 H27 109.5 . . ? H26 C33 H27 109.5 . . ? C34 O3 C33 116.7(8) . . ? O4 C34 O3 123.1(8) . . ? O4 C34 C35 123.4(8) . . ? O3 C34 C35 113.4(7) . . ? C36 C35 C34 121.5(8) . . ? C36 C35 H28 119.3 . . ? C34 C35 H28 119.3 . . ? C35 C36 C37 124.0(9) . . ? C35 C36 H29 118.0 . . ? C37 C36 H29 118.0 . . ? C38 C37 C36 122.1(9) . . ? C38 C37 C47 121.0(8) . . ? C36 C37 C47 116.9(8) . . ? C37 C38 C39 129.8(8) . . ? C37 C38 C46 124.5(8) . . ? C39 C38 C46 105.6(7) . . ? C40 C39 C38 110.5(7) . . ? C40 C39 C53 122.8(8) . . ? C38 C39 C53 126.7(7) . . ? C39 C40 C59 128.9(7) . . ? C39 C40 C41 107.2(7) . . ? C59 C40 C41 123.9(7) . . ? C42 C41 C46 120.1(8) . . ? C42 C41 C40 130.1(8) . . ? C46 C41 C40 109.8(7) . . ? C41 C42 C43 120.2(8) . . ? C41 C42 H30 119.9 . . ? C43 C42 H30 119.9 . . ? C44 C43 C42 119.8(9) . . ? C44 C43 H31 120.1 . . ? C42 C43 H31 120.1 . . ? C43 C44 C45 120.3(9) . . ? C43 C44 H32 119.8 . . ? C45 C44 H32 119.8 . . ? C46 C45 C44 120.1(9) . . ? C46 C45 H33 119.9 . . ? C44 C45 H33 119.9 . . ? C45 C46 C41 119.4(8) . . ? C45 C46 C38 133.7(8) . . ? C41 C46 C38 106.8(7) . . ? C48 C47 C52 119.4(9) . . ? C48 C47 C37 123.2(9) . . ? C52 C47 C37 117.4(7) . . ? C47 C48 C49 120.9(10) . . ? C47 C48 H34 119.5 . . ? C49 C48 H34 119.5 . . ? C48 C49 C50 119.2(9) . . ? C48 C49 H35 120.4 . . ? C50 C49 H35 120.4 . . ? C51 C50 C49 119.2(10) . . ? C51 C50 H36 120.4 . . ? C49 C50 H36 120.4 . . ? C50 C51 C52 122.5(11) . . ? C50 C51 H37 118.7 . . ? C52 C51 H37 118.7 . . ? C51 C52 C47 118.7(8) . . ? C51 C52 H38 120.6 . . ? C47 C52 H38 120.6 . . ? C58 C53 C54 119.7(8) . . ? C58 C53 C39 121.9(8) . . ? C54 C53 C39 118.4(8) . . ? C53 C54 C55 120.3(8) . . ? C53 C54 H39 119.8 . . ? C55 C54 H39 119.8 . . ? C56 C55 C54 119.0(9) . . ? C56 C55 H40 120.5 . . ? C54 C55 H40 120.5 . . ? C57 C56 C55 121.0(8) . . ? C57 C56 H41 119.5 . . ? C55 C56 H41 119.5 . . ? C56 C57 C58 118.9(9) . . ? C56 C57 H42 120.6 . . ? C58 C57 H42 120.6 . . ? C53 C58 C57 121.1(9) . . ? C53 C58 H43 119.5 . . ? C57 C58 H43 119.5 . . ? C64 C59 C60 118.3(9) . . ? C64 C59 C40 122.6(8) . . ? C60 C59 C40 119.0(8) . . ? C59 C60 C61 120.2(9) . . ? C59 C60 H44 119.9 . . ? C61 C60 H44 119.9 . . ? C62 C61 C60 118.4(10) . . ? C62 C61 H45 120.8 . . ? C60 C61 H45 120.8 . . ? C61 C62 C63 122.0(9) . . ? C61 C62 H46 119.0 . . ? C63 C62 H46 119.0 . . ? C64 C63 C62 118.6(9) . . ? C64 C63 H47 120.7 . . ? C62 C63 H47 120.7 . . ? C63 C64 C59 122.2(10) . . ? C63 C64 H48 118.9 . . ? C59 C64 H48 118.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 O2 -5.3(15) . . . . ? C1 O1 C2 C3 171.4(10) . . . . ? O2 C2 C3 C4 -176.5(9) . . . . ? O1 C2 C3 C4 6.9(13) . . . . ? C2 C3 C4 C5 -178.1(9) . . . . ? C3 C4 C5 C6 -176.8(9) . . . . ? C3 C4 C5 C15 7.5(14) . . . . ? C4 C5 C6 C7 -9.2(15) . . . . ? C15 C5 C6 C7 166.5(9) . . . . ? C4 C5 C6 C14 169.5(9) . . . . ? C15 C5 C6 C14 -14.8(14) . . . . ? C5 C6 C7 C8 179.7(9) . . . . ? C14 C6 C7 C8 0.8(10) . . . . ? C5 C6 C7 C21 1.1(15) . . . . ? C14 C6 C7 C21 -177.9(8) . . . . ? C6 C7 C8 C27 -178.9(8) . . . . ? C21 C7 C8 C27 -0.2(14) . . . . ? C6 C7 C8 C9 -0.3(10) . . . . ? C21 C7 C8 C9 178.4(8) . . . . ? C7 C8 C9 C10 -178.7(9) . . . . ? C27 C8 C9 C10 0.0(15) . . . . ? C7 C8 C9 C14 -0.4(10) . . . . ? C27 C8 C9 C14 178.2(8) . . . . ? C14 C9 C10 C11 -0.8(13) . . . . ? C8 C9 C10 C11 177.2(9) . . . . ? C9 C10 C11 C12 -1.1(13) . . . . ? C10 C11 C12 C13 2.0(14) . . . . ? C11 C12 C13 C14 -0.9(13) . . . . ? C12 C13 C14 C9 -1.0(13) . . . . ? C12 C13 C14 C6 -177.7(9) . . . . ? C10 C9 C14 C13 1.9(13) . . . . ? C8 C9 C14 C13 -176.5(8) . . . . ? C10 C9 C14 C6 179.3(8) . . . . ? C8 C9 C14 C6 0.9(10) . . . . ? C5 C6 C14 C13 -3.1(16) . . . . ? C7 C6 C14 C13 175.9(9) . . . . ? C5 C6 C14 C9 180.0(8) . . . . ? C7 C6 C14 C9 -1.1(10) . . . . ? C6 C5 C15 C16 -69.5(11) . . . . ? C4 C5 C15 C16 106.4(9) . . . . ? C6 C5 C15 C20 107.1(10) . . . . ? C4 C5 C15 C20 -77.0(11) . . . . ? C20 C15 C16 C17 -1.1(12) . . . . ? C5 C15 C16 C17 175.6(8) . . . . ? C15 C16 C17 C18 0.0(13) . . . . ? C16 C17 C18 C19 -0.1(15) . . . . ? C17 C18 C19 C20 1.2(15) . . . . ? C16 C15 C20 C19 2.2(13) . . . . ? C5 C15 C20 C19 -174.4(8) . . . . ? C18 C19 C20 C15 -2.2(14) . . . . ? C8 C7 C21 C26 105.2(10) . . . . ? C6 C7 C21 C26 -76.2(12) . . . . ? C8 C7 C21 C22 -79.3(12) . . . . ? C6 C7 C21 C22 99.2(11) . . . . ? C26 C21 C22 C23 0.8(14) . . . . ? C7 C21 C22 C23 -174.8(8) . . . . ? C21 C22 C23 C24 0.0(15) . . . . ? C22 C23 C24 C25 -0.6(14) . . . . ? C23 C24 C25 C26 0.4(13) . . . . ? C24 C25 C26 C21 0.4(14) . . . . ? C22 C21 C26 C25 -1.0(13) . . . . ? C7 C21 C26 C25 174.5(8) . . . . ? C7 C8 C27 C28 -49.0(13) . . . . ? C9 C8 C27 C28 132.6(9) . . . . ? C7 C8 C27 C32 132.7(9) . . . . ? C9 C8 C27 C32 -45.7(12) . . . . ? C32 C27 C28 C29 1.8(12) . . . . ? C8 C27 C28 C29 -176.5(8) . . . . ? C27 C28 C29 C30 -2.3(13) . . . . ? C28 C29 C30 C31 0.4(14) . . . . ? C29 C30 C31 C32 2.1(14) . . . . ? C30 C31 C32 C27 -2.7(13) . . . . ? C28 C27 C32 C31 0.7(11) . . . . ? C8 C27 C32 C31 179.0(7) . . . . ? C33 O3 C34 O4 5.5(16) . . . . ? C33 O3 C34 C35 -171.9(9) . . . . ? O4 C34 C35 C36 175.6(10) . . . . ? O3 C34 C35 C36 -7.0(13) . . . . ? C34 C35 C36 C37 174.4(8) . . . . ? C35 C36 C37 C38 178.3(9) . . . . ? C35 C36 C37 C47 -3.1(13) . . . . ? C36 C37 C38 C39 10.0(15) . . . . ? C47 C37 C38 C39 -168.5(8) . . . . ? C36 C37 C38 C46 -166.5(8) . . . . ? C47 C37 C38 C46 15.0(14) . . . . ? C37 C38 C39 C40 -177.3(9) . . . . ? C46 C38 C39 C40 -0.3(9) . . . . ? C37 C38 C39 C53 1.0(16) . . . . ? C46 C38 C39 C53 178.0(8) . . . . ? C38 C39 C40 C59 -177.1(8) . . . . ? C53 C39 C40 C59 4.5(15) . . . . ? C38 C39 C40 C41 1.3(10) . . . . ? C53 C39 C40 C41 -177.0(7) . . . . ? C39 C40 C41 C42 179.9(9) . . . . ? C59 C40 C41 C42 -1.5(15) . . . . ? C39 C40 C41 C46 -2.0(10) . . . . ? C59 C40 C41 C46 176.6(8) . . . . ? C46 C41 C42 C43 3.0(13) . . . . ? C40 C41 C42 C43 -179.1(9) . . . . ? C41 C42 C43 C44 -0.3(13) . . . . ? C42 C43 C44 C45 -2.1(14) . . . . ? C43 C44 C45 C46 1.7(14) . . . . ? C44 C45 C46 C41 1.1(13) . . . . ? C44 C45 C46 C38 176.4(8) . . . . ? C42 C41 C46 C45 -3.4(13) . . . . ? C40 C41 C46 C45 178.3(7) . . . . ? C42 C41 C46 C38 -179.9(8) . . . . ? C40 C41 C46 C38 1.8(10) . . . . ? C37 C38 C46 C45 0.5(15) . . . . ? C39 C38 C46 C45 -176.7(9) . . . . ? C37 C38 C46 C41 176.3(9) . . . . ? C39 C38 C46 C41 -1.0(9) . . . . ? C38 C37 C47 C48 -106.9(10) . . . . ? C36 C37 C47 C48 74.5(11) . . . . ? C38 C37 C47 C52 70.5(11) . . . . ? C36 C37 C47 C52 -108.1(9) . . . . ? C52 C47 C48 C49 -2.2(13) . . . . ? C37 C47 C48 C49 175.2(8) . . . . ? C47 C48 C49 C50 1.9(14) . . . . ? C48 C49 C50 C51 -1.9(15) . . . . ? C49 C50 C51 C52 2.3(15) . . . . ? C50 C51 C52 C47 -2.5(14) . . . . ? C48 C47 C52 C51 2.4(12) . . . . ? C37 C47 C52 C51 -175.1(8) . . . . ? C40 C39 C53 C58 -107.0(11) . . . . ? C38 C39 C53 C58 74.9(11) . . . . ? C40 C39 C53 C54 76.4(10) . . . . ? C38 C39 C53 C54 -101.6(11) . . . . ? C58 C53 C54 C55 -1.6(13) . . . . ? C39 C53 C54 C55 175.1(8) . . . . ? C53 C54 C55 C56 -0.1(13) . . . . ? C54 C55 C56 C57 0.9(13) . . . . ? C55 C56 C57 C58 0.0(13) . . . . ? C54 C53 C58 C57 2.5(13) . . . . ? C39 C53 C58 C57 -174.0(8) . . . . ? C56 C57 C58 C53 -1.7(13) . . . . ? C39 C40 C59 C64 44.8(14) . . . . ? C41 C40 C59 C64 -133.4(9) . . . . ? C39 C40 C59 C60 -131.7(10) . . . . ? C41 C40 C59 C60 50.0(12) . . . . ? C64 C59 C60 C61 5.4(13) . . . . ? C40 C59 C60 C61 -177.8(8) . . . . ? C59 C60 C61 C62 -1.9(13) . . . . ? C60 C61 C62 C63 -1.7(14) . . . . ? C61 C62 C63 C64 1.5(14) . . . . ? C62 C63 C64 C59 2.4(13) . . . . ? C60 C59 C64 C63 -5.8(13) . . . . ? C40 C59 C64 C63 177.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.375 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.091 data_qq _database_code_depnum_ccdc_archive 'CCDC 926859' #TrackingRef '2g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 O4' _chemical_formula_weight 346.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.675(3) _cell_length_b 5.0054(8) _cell_length_c 14.303(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.451(12) _cell_angle_gamma 90.00 _cell_volume 826.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 1660 _cell_measurement_theta_min 3.5919 _cell_measurement_theta_max 25.3458 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9858 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4986 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1433 _reflns_number_gt 1153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.8450P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1433 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0890(2) 0.2605(5) 0.40558(16) 0.0273(6) Uani 1 1 d . . . C2 C 0.1428(2) 0.4707(5) 0.46177(16) 0.0285(6) Uani 1 1 d . . . C3 C 0.2587(2) 0.5363(5) 0.45853(17) 0.0291(6) Uani 1 1 d . . . H1 H 0.2951 0.6787 0.4955 0.035 Uiso 1 1 calc R . . C4 C 0.3194(2) 0.3863(5) 0.39928(16) 0.0278(6) Uani 1 1 d . . . H2 H 0.3982 0.4270 0.3959 0.033 Uiso 1 1 calc R . . C5 C 0.2657(2) 0.1794(5) 0.34568(17) 0.0286(6) Uani 1 1 d . . . H3 H 0.3085 0.0781 0.3065 0.034 Uiso 1 1 calc R . . C6 C 0.1496(2) 0.1170(5) 0.34815(17) 0.0291(6) Uani 1 1 d . . . H4 H 0.1133 -0.0239 0.3103 0.035 Uiso 1 1 calc R . . C7 C -0.0344(2) 0.2349(5) 0.42125(16) 0.0278(6) Uani 1 1 d . . . C8 C -0.0525(2) 0.4215(5) 0.48526(17) 0.0282(6) Uani 1 1 d . . . C9 C -0.1156(2) 0.0361(5) 0.36937(17) 0.0273(6) Uani 1 1 d . . . O1 O -0.08756(16) -0.1240(4) 0.31648(13) 0.0375(5) Uani 1 1 d . . . O2 O -0.22462(16) 0.0659(3) 0.38772(11) 0.0322(5) Uani 1 1 d . . . C10 C -0.3099(2) -0.1162(5) 0.33483(17) 0.0303(6) Uani 1 1 d . . . H5 H -0.2897 -0.3040 0.3516 0.036 Uiso 1 1 calc R . . H6 H -0.3104 -0.0934 0.2660 0.036 Uiso 1 1 calc R . . C11 C -0.4266(2) -0.0492(6) 0.3606(2) 0.0419(7) Uani 1 1 d . . . H7 H -0.4255 -0.0759 0.4286 0.063 Uiso 1 1 calc R . . H8 H -0.4853 -0.1657 0.3255 0.063 Uiso 1 1 calc R . . H9 H -0.4452 0.1376 0.3445 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0285(12) 0.0283(14) 0.0247(12) 0.0090(10) 0.0028(10) 0.0041(11) C2 0.0333(13) 0.0302(14) 0.0232(12) 0.0099(10) 0.0086(10) 0.0120(11) C3 0.0391(14) 0.0252(13) 0.0218(12) 0.0020(10) 0.0000(10) 0.0025(11) C4 0.0264(12) 0.0297(14) 0.0279(13) 0.0021(10) 0.0056(10) -0.0006(10) C5 0.0308(13) 0.0305(14) 0.0250(12) 0.0008(10) 0.0058(10) 0.0039(10) C6 0.0308(13) 0.0287(14) 0.0268(12) 0.0036(10) 0.0014(10) 0.0003(10) C7 0.0318(13) 0.0253(13) 0.0254(12) 0.0031(10) 0.0012(10) 0.0007(10) C8 0.0376(14) 0.0219(13) 0.0231(12) 0.0058(10) -0.0021(10) 0.0007(10) C9 0.0265(12) 0.0288(14) 0.0242(12) 0.0063(10) -0.0040(10) -0.0008(10) O1 0.0361(10) 0.0337(11) 0.0410(11) -0.0066(9) 0.0003(8) -0.0013(8) O2 0.0442(11) 0.0271(10) 0.0238(9) -0.0053(7) 0.0000(8) -0.0020(8) C10 0.0326(13) 0.0324(14) 0.0247(13) -0.0030(10) -0.0003(10) -0.0026(11) C11 0.0396(15) 0.0489(18) 0.0380(15) 0.0022(13) 0.0082(12) -0.0002(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.365(3) . ? C1 C2 1.414(4) . ? C1 C7 1.496(3) . ? C2 C3 1.399(4) . ? C2 C8 1.487(3) 3_566 ? C3 C4 1.401(3) . ? C3 H1 0.9500 . ? C4 C5 1.383(4) . ? C4 H2 0.9500 . ? C5 C6 1.396(3) . ? C5 H3 0.9500 . ? C6 H4 0.9500 . ? C7 C8 1.346(3) . ? C7 C9 1.494(3) . ? C8 C8 1.466(5) 3_566 ? C8 C2 1.487(3) 3_566 ? C9 O1 1.181(3) . ? C9 O2 1.345(3) . ? O2 C10 1.474(3) . ? C10 C11 1.501(4) . ? C10 H5 0.9900 . ? C10 H6 0.9900 . ? C11 H7 0.9800 . ? C11 H8 0.9800 . ? C11 H9 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.5(2) . . ? C6 C1 C7 129.9(2) . . ? C2 C1 C7 109.6(2) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 C8 133.8(2) . 3_566 ? C1 C2 C8 105.7(2) . 3_566 ? C2 C3 C4 118.2(2) . . ? C2 C3 H1 120.9 . . ? C4 C3 H1 120.9 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H2 119.7 . . ? C3 C4 H2 119.7 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H3 119.5 . . ? C6 C5 H3 119.5 . . ? C1 C6 C5 119.2(2) . . ? C1 C6 H4 120.4 . . ? C5 C6 H4 120.4 . . ? C8 C7 C9 130.4(2) . . ? C8 C7 C1 107.1(2) . . ? C9 C7 C1 122.5(2) . . ? C7 C8 C8 111.1(3) . 3_566 ? C7 C8 C2 142.4(2) . 3_566 ? C8 C8 C2 106.5(3) 3_566 3_566 ? O1 C9 O2 124.1(2) . . ? O1 C9 C7 123.7(2) . . ? O2 C9 C7 112.2(2) . . ? C9 O2 C10 114.71(19) . . ? O2 C10 C11 107.7(2) . . ? O2 C10 H5 110.2 . . ? C11 C10 H5 110.2 . . ? O2 C10 H6 110.2 . . ? C11 C10 H6 110.2 . . ? H5 C10 H6 108.5 . . ? C10 C11 H7 109.5 . . ? C10 C11 H8 109.5 . . ? H7 C11 H8 109.5 . . ? C10 C11 H9 109.5 . . ? H7 C11 H9 109.5 . . ? H8 C11 H9 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(3) . . . . ? C7 C1 C2 C3 -179.2(2) . . . . ? C6 C1 C2 C8 -179.6(2) . . . 3_566 ? C7 C1 C2 C8 0.6(2) . . . 3_566 ? C1 C2 C3 C4 -0.8(3) . . . . ? C8 C2 C3 C4 179.5(2) 3_566 . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? C7 C1 C6 C5 -180.0(2) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C6 C1 C7 C8 179.5(2) . . . . ? C2 C1 C7 C8 -0.7(3) . . . . ? C6 C1 C7 C9 -2.0(4) . . . . ? C2 C1 C7 C9 177.9(2) . . . . ? C9 C7 C8 C8 -178.0(2) . . . 3_566 ? C1 C7 C8 C8 0.4(3) . . . 3_566 ? C9 C7 C8 C2 1.9(5) . . . 3_566 ? C1 C7 C8 C2 -179.7(3) . . . 3_566 ? C8 C7 C9 O1 -177.6(3) . . . . ? C1 C7 C9 O1 4.2(4) . . . . ? C8 C7 C9 O2 4.3(4) . . . . ? C1 C7 C9 O2 -173.9(2) . . . . ? O1 C9 O2 C10 -1.0(3) . . . . ? C7 C9 O2 C10 177.09(19) . . . . ? C9 O2 C10 C11 -177.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.709 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.061